Category: 4630-80-2

Reference of 4630-80-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 4630-80-2 name is Methyl cyclopentanecarboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A 2.5 M solution of BuLi in hexane (2.77 mmol; 1.1 ml; 1.2 eq) is added at -10 C. to a solution of DIPA (diisopropylethylamine) (3 mmol; 1.3 eq; 420 mul) in THF (9 ml) under inert atmosphere. The mixture is stirred for 1 hour at 0 C. This LDA solution, freshly prepared, is added dropwise to a solution of cyclopentanoic acid methyl ester in 5 ml of THF at -55 C. The mixture is stirred for 1 hour at -55 C. under inert atmosphere. HMPA (hexylmethylphophoramide) (3.46 mmol; 1.5 eq; 610 mul) is added and the mixture is stirred for 10 minutes at the same temperature. A solution of 4-methoxybenzyl mercaptan disulfide (3 mmol; 1.3 eq; 920 mg) in 12 ml of THF is then added dropwise at -55 C. After returning to room temperature, the mixture is stirred overnight. The mixture is partitioned between 10 ml of saturated NH4Cl and 20 ml of AcOEt. The organic phase is washed with saturated NH4Cl (2×10 ml), saturated NaCl (2×15 ml), dried on Na2SO4 and then concentrated under reduced pressure to yield the crude product which is purified by chromatography on silica gel. (0262) C(R2R3)=Cyclopentyl: oil (Yield: 40%) (0263) HPLC: Atlantis T3, CH3CN (0.1% TFA)/H2O (0.1% TFA) Gradient 30-90% 10 min, Rt=9.68 min (0264) NMR (CDCl3, 200 MHz): 1.60-2.40 (8H, m); 3.67 (3H, s); 3.77 (2H, s); 3.80 (3H, s); 6.83 (2H, d); 7.24 (2H, d)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl cyclopentanecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; PHARMALEADS; ROQUES, Bernard Pierre; FOURNIE-ZALUSKI, Marie-Claude; PORAS, Herve; US2015/299116; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 4630-80-2, name is Methyl cyclopentanecarboxylate, molecular formula is C7H12O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: Methyl cyclopentanecarboxylate

Example 230 Preparation of 1-(3-Butenyl)cyclopentane Carboxylic Acid Methyl Ester To a solution of diisopropylamine (225 mmol, 31.6 mL) in THF (150 mL) was added dropwise a solution of n-butyl lithium (217.5 mmol, 87 mL, 2.5M) in hexanes at -10 C. while maintaining the temperature below 0 C. After addition, the solution was stirred for 30 min at 0 C. To this, a solution of methyl cyclopentane carboxylate (150 mmol, 19.23 g) in THF (30 mL) was added dropwise at -70 C. maintaining the internal temperature between -60 to -70 C. After addition, the reaction mixture was stirred for 1 h at -50 to -60 C. Then, a solution of 4-bromo-1-butene (142.2 mmol, 19.2 g) in THF (30 mL) was added dropwise and the light brown suspension was stirred for 1 h at -60 to -70 C. Then, it was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into a saturated solution of ammonium chloride (250 mL) and the mixture was extracted with ether (2*150 mL). The combined extracts were washed with a saturated solution of sodium chloride (150 mL) and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the solution was concentrated under vacuum and the residue was distilled at 63-67 C./2.5 mm Hg to give 13.77 g (53%) of a colorless oil. HR MS (C11H16O2): Obs mass, 182.1311. Calcd mass, 182.1307 (M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4630-80-2, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; US6455550; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 4630-80-2,Some common heterocyclic compound, 4630-80-2, name is Methyl cyclopentanecarboxylate, molecular formula is C7H12O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A 50-mL glass reactor was charged under dry argon at 0 C with 15 mL of THF, and 20 mmol of magnesium powder, 20 mmol of EtAlCl2, and 1.0 mmol of Cp2TiCl2 were added in succession under stirring. After 1 h, 10 mmol of symmetrical acetylene and 20 mmol of ester were added, and the mixture was heated to 60 C and stirred for 6 h at that temperature. When the reaction was complete, the mixture was cooled to 0 C in a stream of argon, 10-15 mL of diethyl ether was added, and the mixture was hydrolyzed with 5 % aqueous HCl. The organic layer was separated, the aqueous layer was extracted with two portions of diethyl ether, and the combined extracts were washed with a solution of NaHCO3 until neutral washings and dried over MgSO4. The product was isolated by vacuum distillation.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl cyclopentanecarboxylate, its application will become more common.

Reference:
Article; Khafizova; Shaibakova; Chobanov; Gubaidullin; Tyumkina; Dzhemilev; Russian Journal of Organic Chemistry; vol. 51; 9; (2015); p. 1277 – 1281; Zh. Org. Khim.; vol. 51; 9; (2015); p. 1303 – 1307,5;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 4630-80-2, The chemical industry reduces the impact on the environment during synthesis 4630-80-2, name is Methyl cyclopentanecarboxylate, I believe this compound will play a more active role in future production and life.

To LDA (17.03 ml, 17.03 mmol) (1M in THF) at 0 oc was addedmethyl cyclopentanecarboxylate (1.75 g, 13.6 mmol) and the mixture stirred for 5 min. Asolution of 4-(bromomethyl)-1-chloro-2-(3-methoxypropoxy)benzene (2 g, 6.8 mmol) in THF(5ml) was added dropwise then the mixture was allow to warm toRT. The mixture wasquenched with ice and NH4CI (aq), and then extracted with EtOAc. The organics werecombined, dried (brine, Na2S04), and concentrated to an oil. The oil was purified on silicagel hex:EtOAc (eluting at -1 0%) to give methyl 1-(4-chloro-3-(3- methoxypropoxy)benzyl)cyclopentane-1-carboxylate (2.28 g, 6.69 mmol, 98% yield) as ayellow oil. LCMS (ESI) (m/z): 363.3 (M+23t.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl cyclopentanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CATALANO, John G.; DICKSON, Hamilton D.; KAZMIERSKI, Wieslaw Mieczyslaw; LEIVERS, Martin R.; WEATHERHEAD, John Gordon; (389 pag.)WO2018/154466; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 4630-80-2,Some common heterocyclic compound, 4630-80-2, name is Methyl cyclopentanecarboxylate, molecular formula is C7H12O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 168 Preparation of 1-(4-Bromobutyl)cyclopentane Carboxylic Acid Methyl Ester To a solution of diisopropylamine (150 mmol, 21 mL) in THF (100 mL) was added dropwise a solution of n-butyl lithium (145 mmol, 58 mL, 2.5M) in hexanes at -10 C. while maintaining the temperature below 0 C. After addition, the solution was stirred for 30 min at 0 C. To this a solution of methyl cyclopentane carboxylate (100 mmol, 13.1 g) in THF (20 mL) was added dropwise at -70 C. maintaining the internal temperature between -60 to -70 C. After addition, the reaction mixture was stirred for 1 h at -50 to -60 C. Then, a solution of 1,4-dibromobutane (100 mmol, 21.59 g) in THF (20 mL) was added dropwise and the light brown suspension was stirred for 1 h at -60 to -70 C. Then, it was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into a saturated solution of ammonium chloride (200 mL) and the organic compound was extracted into ether (2*100 mL). The combined extracts were washed with a saturated brine solution (150 mL) and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the solution was concentrated under vacuum and the resulting residue was distilled at 120-133 C./2.5 mm Hg to obtain 1-(4-bromobutyl)cyclopentane carboxylic acid methyl ester as a colorless oil (12.8 g, 48%). HR MS (C11H19BrO2): Obs mass, a 262.0565. Calcd mass, 262.0568 (M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl cyclopentanecarboxylate, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; US6455550; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 4630-80-2,Some common heterocyclic compound, 4630-80-2, name is Methyl cyclopentanecarboxylate, molecular formula is C7H12O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 168 Preparation of 1-(4-Bromobutyl)cyclopentane Carboxylic Acid Methyl Ester To a solution of diisopropylamine (150 mmol, 21 mL) in THF (100 mL) was added dropwise a solution of n-butyl lithium (145 mmol, 58 mL, 2.5M) in hexanes at -10 C. while maintaining the temperature below 0 C. After addition, the solution was stirred for 30 min at 0 C. To this a solution of methyl cyclopentane carboxylate (100 mmol, 13.1 g) in THF (20 mL) was added dropwise at -70 C. maintaining the internal temperature between -60 to -70 C. After addition, the reaction mixture was stirred for 1 h at -50 to -60 C. Then, a solution of 1,4-dibromobutane (100 mmol, 21.59 g) in THF (20 mL) was added dropwise and the light brown suspension was stirred for 1 h at -60 to -70 C. Then, it was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into a saturated solution of ammonium chloride (200 mL) and the organic compound was extracted into ether (2*100 mL). The combined extracts were washed with a saturated brine solution (150 mL) and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the solution was concentrated under vacuum and the resulting residue was distilled at 120-133 C./2.5 mm Hg to obtain 1-(4-bromobutyl)cyclopentane carboxylic acid methyl ester as a colorless oil (12.8 g, 48%). HR MS (C11H19BrO2): Obs mass, a 262.0565. Calcd mass, 262.0568 (M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl cyclopentanecarboxylate, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; US6455550; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 4630-80-2, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4630-80-2, name is Methyl cyclopentanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Synthesis of methyl 1-methylcyclopentanecarboxylate:To a solution of di-isopropylamine (69 ml) in tetrahydrafuran (100 ml), n- BuLi (166 ml) in hexane was added at 0 C and the reaction mixture was allowed to stir at same temperature for about 10-15 minutes. The reaction mixture was stirred at room temperature for about 45 minutes. Methyl cyclopentanecarboxylate (25 g) in tetrahydrafuran (200 ml) was added drop-wise at -78 C to above reaction mixture. The reaction mixture was stirred at same temperature for about 2 hours and then methyl iodide was added drop-wise. The reaction was maintained at -78C for an hour and allowed to attain room temperature. The reaction mixture was stirred overnight at room temperature and quenched at 0 C with saturated aq. NH4C1 solution and the compound was extracted with ethyl acetate. The organic layer was washed with saturated brine solution, dried over anhydrous Na2S04 and concentrated. Crude product was directly used for the next step. 1H NMR (CDC13, 300 MHz): 3.66 (s, 3H), 2.10- 2.03 (m, 2H), 1.69- 1.64 (m, 4H), 1.50- 1.42 (m, 2H), 1.23 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis Methyl cyclopentanecarboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; HETERO RESEARCH FOUNDATION; PARTHASARADHI REDDY, Bandi; MANOHAR SHARMA, Vedula; RATHNAKAR REDDY, Kura; VL SUBRAHMANYAM, Lanka; SUDHAKAR, Neela; WO2012/25857; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4630-80-2, name is Methyl cyclopentanecarboxylate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 4630-80-2, category: esters-buliding-blocks

General procedure: Into an oven-dried reaction vial flushed with N2 were taken esters 8 (0.60 mmol) and anhydrous toluene (3.0 mL). The reaction vial was cooled to -78C and LDA (2M in THF, 0.36 mL) was added dropwise with stirring. After 1h at -78C, sulfinylimine 7 (0.5 mmol) dissolved in anhydrous toluene (2.0 mL) was added dropwise. Stirring was continued for 2 h with the temperature gradual rising to room temperature, then the reaction was quenched with saturated H2O (3.0 mL). The organic layer was taken and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered and the solvent was removed to give the crude product 9, which was purified by column chromatography (hexane/EtOAc, 4:1).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl cyclopentanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dai, Yanling; Xie, Chen; Mei, Haibo; Han, Jianlin; Soloshonok, Vadim A.; Pan, Yi; Tetrahedron; vol. 71; 51; (2015); p. 9550 – 9556;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 4630-80-2,Some common heterocyclic compound, 4630-80-2, name is Methyl cyclopentanecarboxylate, molecular formula is C7H12O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

EXAMPLE 61 120N-(5-(l-piperazinyl)-2-pyridinyl)spiro[cyclopentane-l,9′- pyrido [4′,3′ :3,4] cyclopenta[l,2-d] pyrimidin]-2′-amine 1212-(3-Bromo-4-pyridinyl)-l-cyclopentylethanone (121) Under a nitrogen atmosphere LiHMDS (LOM solution in tetrahydrofuran, 49.6 ml, 49.6 mmol) was added to a solution of methyl cyclopentanecarboxylate (3.630 g, 28.3 mmol) and 3-bromo-4-methylpyridine (2.62 ml, 23.6 mmol) in 10ml of anhydrous THF over a period of 5min at -780C. AfterlOmin the solution was allowed to warm to 2O0C and stirred for 2hours. The solution was then cooled in ice water, before the pH was adjusted to 4.5 with 25% citric acid. After extraction with DCM the organic layer was dried over Na2SO4 and then concentrated to afford 2-(3-bromo-4-pyridinyl)-l-cyclopentylethanone (121) (6.86g, crude). 1H NMR (500 MHz, DMSO-d6) delta 8.68 (IH, s), 8.48 (IH, d, J = 4.9Hz), 7.37 (H, d, J = 4.9 Hz), 4.07 (2H, s), 3.08 (IH, ddd, Jl = 16.1 Hz, J2 = 7.3 Hz, J3 = 1.2 Hz), 1.80- 1.85 (2H, m), 1.72-1.77 (2H, m), 1.55-1.59 (4H, m); LCMS-ESI (POS), M/Z, M+l : Found 268.0

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl cyclopentanecarboxylate, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2009/126584; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 4630-80-2, The chemical industry reduces the impact on the environment during synthesis 4630-80-2, name is Methyl cyclopentanecarboxylate, I believe this compound will play a more active role in future production and life.

prparation of intermediate 6A:l-((benzyloxy)methyl)cyclopentanecarboxylic acid methyl esterCyclopentanecarboxylic acid methyl ester (1.28 g, 10 mmol) was dissolved in 20 mL of tetrahydrofuran, to which was added dropwise a tetrahydrofuran solution of KHMDS (3.0 g, 15 mmol) at -78 C under nitrogen protection. After the addition was completed, the reaction proceeded at -78 C for further 30 min, after which benzyl chloromethyl ether (2.03 g, 13 mmol) was added. The reaction solution was allowed to warm up to room temperature and reacted overnight. Water was added and the reaction solution was extracted with ethyl acetate. The organic phase was combined, dried, filtered, and rotary evaporated to give 1.69 g of colorless liquid 6A. Yield: 68.1%. The crude product was used directly in the next step without further purification.MS (ESI, m/z): [M+H]+: 249.1.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl cyclopentanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BEIJING HANMI PHARMACEUTICAL CO., LTD; ZHANG, Bo; YANG, Jun; LIU, Jinming; HUANG, Hai; WU, Yong; TAO, Ran; XU, Jiangcheng; SHEN, Ning; MOON, Sunghwan; KIM, Maengsup; WO2013/56679; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics