Category: 87661-20-9

Electric Literature of 87661-20-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of (-R NH (4.74 mL, 33.2 mmol) in THF (40 mL) at 0C was added n-BuLi (13.3 mL of a 2.5M solution in hexanes, 33.2 mmol) portionwise. The LDA solution was stirred for 15 min at 0C, then was warmed to RT, and stirred for 30 min at RT, then was cooled to-78C. Tert-butyl cyclopropanecarboxylate (3.78 g, 26.6 mmol) was added dropwise over 10 min. The reaction was stirred at -78C for 2 h, after which l-bromopropane (4.84 mL, 53.2 mmol) was added dropwise over 20 min. The reaction was allowed to slowly warm to RT and stirred overnight at RT, then was quenched with satd aq. NH4Cl and extracted with EtOAc (2x). The combined organic extracts were washed with brine, dried (MgSCri), and concentrated in vacuo. The residue was distilled under reduced pressure (20 torr, BP = 95C) to give the title compound (2.99 g, 61 % yield) as an oil. NMR (500 MHz, CDCb) d 1.48 (m, 4H), 1.45 (s, 9H), 1.12 (m, 2H), 0.92 (m, 3H), 0.61 (m, 2H).

The synthetic route of tert-Butyl cyclopropanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHENG, Peter Tai Wah; KALTENBACH III, Robert F.; SHI, Jun; SHI, Yan; ZHANG, Hao; (0 pag.)WO2020/60915; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 87661-20-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 72 (2S)-1-({1-[2-(3-Chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-cyclopropylamino}-acetyl)-pyrrolidine-2-carbonitrile The title compound was prepared in analogy to example 60 starting from 4-chloromethyl-5-methyl-2-(3-chloro-phenyl)-oxazole and tert.butyl cyclopropanecarboxylate. The starting material could be prepared from 3-methylbenzaldehyde and 2,3-butanedione oxime as described for benzaldehyde in Chem. Pharm. Bull. 1971, 19, 2050-2057. Steps A] and C] were performed as outlined in example 60, step B] was done according to example 69. The title compound was obtained as a brown gum. MS (ISP): 399.3 (MH+) and 401.3 (MH+).

The synthetic route of tert-Butyl cyclopropanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer, Markus; Hunziker, Daniel; Kuehne, Holger; Loeffler, Bernd M.; Sarabu, Ramakanth; Wessel, Hans P.; US2003/130281; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C8H14O2

To a solution of 1M LDA (42.1 mmol, 42.1 mL) at – 78 C was added dropwise t-butylcyclopropane carboxylate (5.0 g, 35.1 mmol) in 70 mL THF. After 1.5 hours, a solution of allyl bromide (3.03 mL, 35.1 mmol) in 10 mL THF was added. The reaction mixture was allowed to warm slowly to room temperature. After 18 hours, the reaction was quenched with saturated NH4CI (aq), and partitioned between EtOAc and H2O. The organic and aqueous layers were separated, and the aqueous layer was washed with 2 c 20 mL ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified on an 80 g silacel column, eluting with 0-15% EtOAc/hexanes. The product fractions were concentrated in vacuo to yield 1-allyl-cyclopropanecarboxylic acid tert-butyl ester, 2.48 g (38% yield). 1H NMR (CHLOROFORM-d) d: 5.73-6.01 (m, 1H), 4.91-5.13 (m, 2H), 2.27 (dt, J=6.6, 1.3 Hz, 2H), 1.42 (s, 9H), 0.99-1.20 (m, 2H), 0.49-0.73 (m, 2H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BIOHAVEN PHARMACEUTICAL HOLDING COMPANY LTD.; CONWAY, Charles M.; DUBOWCHIK, Gene M.; PELLETIER, Jeffery Claude; REITZ, Allen B.; (186 pag.)WO2020/77038; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 87661-20-9, These common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, its 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.

Step 1-A solution of n-butyl lithium in hexane (1.4M, 16.9 mL, 0.09 mol) was added drop wise to a solution of freshly distilled diisopropylamine (3.1 mL, 0.02 mol) in dry THF (20 mL) at -60 C. under a nitrogen atmosphere. The reaction mixture was slowly warmed to -20 C. and stirred for 30 min. The reaction mixture was re-cooled to -60 C. and cyclopropanecarboxylic acid tert-butyl ester (3.1 g, 0.02 mol) was added drop wise over a period of 10 min. The reaction mixture was slowly warmed to -20 C. and stirred for 30 min. To the re-cooled (-60 C.) above reaction mixture was added drop wise 1,8-dibromoctane (2.0 g, 7.0 mmol) in dry THF (5 mL) and DMPU (0.46 mL, 3.2 mmol). Then, the temperature was allowed to reach room temperature and stirred at the same temperature over a period of 16 hours. The resulting reaction mixture was quenched with saturated NH4Cl (50 mL) at 0 C. and the reaction mixture extracted with ether (50 mL×3). The organic phases were combined, dried over anhydrous Na2SO4 and volatiles evaporated under reduced pressure to yield a pale, yellow liquid which was filtered through a silica gel (230-400) column (1.5% ethyl acetate in pet ether) to yield 1.96 g of a crude (70%) colorless oil. The compound was taken to the next step without further purification or characterization.

The synthetic route of 87661-20-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KAREUS THERAPEUTICS, SA; US2012/71528; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 87661-20-9, 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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Under argon, 1.28 ml (9.15 mmol) of diisopropylamine were initally charged in 6 ml of dry THF, and the mixture was cooled to -40 C. 4.26 ml (9.15 mmol) of n-butyllithium solution (2.5 M in hexane) were slowly added dropwise, and the mixture was stirred for 30 min. The reaction solution was then cooled to -78 C., and a solution of 1.30 g (9.15 mmol) of tert-butyl cyclopropanecarboxylic acid in 2 ml of THF was added. After 4 h of stirring at -78 C., a solution of 2.00 g (8.69 mmol) of 1-(bromomethyl)-2-methyl-3-nitrobenzene in 2 ml of THF was added. Slowly, the reaction mixture was warmed to RT overnight. Ammonium chloride solution was then added carefully, and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/dichloromethane 50:1, then 5:1). This gave 0.78 g (29.3% of theory) of the title compound.1H-NMR (400 MHz, DMSO-d6): delta=7.61 (d, 1H), 7.54 (d, 1H), 7.39 (t, 1H), 2.96 (s, 2H), 2.26 (s, 3H), 1.26 (s, 9H), 1.20 (q, 2H), 0.79 (q, 2H).

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

Reference:
Patent; BAYER SCHERING PHARMA AKTIEGESELLSCHAFT; US2011/34450; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 87661-20-9, A common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, its 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.

To a solution of LDA in THF (40 mL of a 0.8 M solution; 33.2 mmol) at -78 C. was added tert-butyl cyclopropane carboxylate (3.78 g, 26.6 mmol) dropwise over 10 min. The solution was stirred at -78 C. for 2 h, after which 1-bromopropane (4.84 mL, 53.2 mmol) was added dropwise over 20 min at -78. The reaction was allowed to slowly warm to RT and stirred overnight at RT, then was quenched with sat’d aq. NH4Cl and extracted with EtOAc (2*). The combined organic extracts were washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was distilled under reduced pressure (20 torr, BP=95 C.) to give the title compound (2.99 g, 61% yield) as an oil. 1H NMR (500 MHz, CDCl3) delta 1.48 (m, 4H), 1.45 (s, 9H), 1.12 (m, 2H), 0.92 (m, 3H), 0.61 (m, 2H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, YAN; Cheng, Peter Tai Wah; Wang, Ying; Shi, Jun; Tao, Shiwei; Li, Jun; Kennedy, Lawrence J.; Kaltenbach, III, Robert F.; Zhang, Hao; Corte, James R.; US2019/185446; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of tert-Butyl cyclopropanecarboxylate

15.9 ml (1.15 equiv.) diisopropylamine were dissolved in 65 ml tetrahydrofuran and cooled to ca -10 C. 65 ml (1.08 equiv.) 1.6 M butyllithium solution in hexane were added over 25 min, maintaining the temperature between -10 C. and 0 C. After 50 nm in at ca. -5 C., the reaction mixture was cooled to -75 C. A solution of 15 g (96.7 mmol, 1 equiv., 92% w/w purity) cyclopropanecarboxylic acid tert-butyl ester in 20 ml tetrahydrofuran was added over 15 min keeping the temperature between -75 C. and -70 C. The reaction mixture was stirred 5 h at -75 C. (milky reaction mixture obtained after 2.5 h). A solution of 12.87 g (1.10 equiv.) allyl bromide was added over 20 min keeping the temperature between -75 C. and -60 C. The reaction mixture was stirred at -78 C. for 1 h, warmed to room temperature and stirred overnight. The reaction mixture was cooled to 0 C. 100 ml sat. aq. ammonium chloride solution were added followed by 30 ml water providing a clear biphasic mixture. The mixture was extracted 3 times with 50 ml tert-butyl methyl ether. The organic phases were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure (40 C./20 mbar) to afford 16.44 g of crude product. The crude product was distilled (2 mbar; ca 40 C. distillation head temperature) to provide the title compound in ca 65% yield.

The synthetic route of 87661-20-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aebi, Johannes; Binggeli, Alfred; Green, Luke; Hartmann, Guido; Maerki, Hans P.; Mattei, Patrizio; Ricklin, Fabienne; US2009/23713; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H14O2

To a cooled solution (-40 C) of DIPEA (4.1 mL, 29.57 mmol, 2.1 eq) in THF (25 mL), was added w-BuLi (2.5M in hexanes, 1 1.2 mL, 28.36 mmol, 2 eq.) drop wise and the mixture was then stirred for 0.5 hr and then cooled to -78 C. Next, a solution of tert-butyl cyclopropanecarboxylate (2 g, 14.08 mmol, 1 eq.) in THF (5 mL) was added and the reaction mixture was stirred for 4 h at -78 C. 1-Propene, 3-bromo- (3.6 mL 42.25 mmol, 3 eq.) was added and reaction mixture was stirred for 2 h at -78 C. The reaction was then quenched with NH4Cl (30 mL) and extracted with DCM. The organic layer was dried over Na2S04 and concentrated to give tert-butyl 1-allylcyclopropane-l -carboxylate (1.5 g, 58 %). 1H NMR: (400 MHz, CDCl3) delta: 5.92-5.81 (m, 1H), 5.07-5.00 (m, 2H), 2.28 (d, J = 6.8 Hz, 2H), 1.45 (s, 9H), 1.15 (dd, J = 4.0, 3.2 Hz, 2H), 0.67 (dd, 4.0, 2.8 Hz, 2H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 87661-20-9.

Reference:
Patent; CAVION, INC.; RICHARDSON, Thomas E.; HIGGIN, Michelle; MACDONALD, Timothy; (102 pag.)WO2018/152317; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 87661-20-9,Some common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, 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.

Step 1: A solution of n-butyl lithium in hexane (1.4M, 95.7 mL, 0.13 mol) was added drop wise to a solution of freshly distilled diisopropylamine (18.75 mL, 0.12 mol) in dry THF (400 mL) at -60 C. under nitrogen atmosphere. The reaction mixture was slowly warmed to -20 C. and stirred for 30 min. The reaction mixture was re-cooled to -60 C. and cyclopropanecarboxylic acid tert-butyl ester (17.34 g, 0.12 mol) added drop wise over a period 30 min. Reaction mixture was slowly warmed to -20 C. and stirred for 30 min. To the re-cooled (-60 C.) reaction mixture was added drop wise 1,12-dibromododecane (40.0 g, 0.12 mol) in dry THF (40 mL) and DMPU (3.12 g, 0.02 mol). Then the temperature was allowed to reach room temperature and stirred at same temperature over a period of 16 h. The resulting reaction mixture was quenched with saturated NH4Cl (500 mL) at 0 C. and the reaction mixture was extracted with ethyl acetate (400 mL×3). The organic phases were combined, dried over anhydrous Na2SO4 and volatiles were evaporated under reduced pressure to yield a pale yellow liquid which was purified through silica gel (230-400) column (0.5% ethyl acetate in petroleum ether) to give product as pale yellow liquid 14.0 g (29%).1H NMR (300 MHz, DMSO-d6) delta (ppm): 1.55-1.61 (m, 2H), 1.08-1.12 (m, 2H), 1.35 (bs, 13H), 1.49 (bs, 16H), 1.64-1.89 (m, 2H), 3.42 (t, J=6.9 Hz, 2H).

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

Reference:
Patent; KAREUS THERAPEUTICS, SA; US2012/71528; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 87661-20-9,Some common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, 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 4ATert-Butyl(+/-)-1-(4-bromopentyl)cyclopropanecarboxylate 21.2 ml (52.7 mmol) of a 2.5 M solution of n-butyllithium in n-hexane were added dropwise to a solution, cooled to -78 C., of 7.4 ml (52.7 mmol) of diisopropylamine in 20 ml of abs. THF. During the addition, the reaction temperature was kept below -60 C. After 30 min of stirring at -60 C. to -70 C., this solution was added dropwise to a solution, cooled to -78 C., of 5.0 g (35.2 mmol) of tert-butyl cyclopropanecarboxylate and 16.2 g (70.3 mmol) of 1,4-dibromopentane in 20 ml of abs. THF. After the end of the addition, cooling was removed and the mixture was slowly warmed to RT with stirring. After a further 4 h of stirring at RT, the reaction mixture was added to saturated aqueous ammonium chloride solution. The mixture was extracted three times with dichloromethane. The combined organic phases were dried over magnesium sulfate and concentrated under reduced pressure. The product was purified by chromatography on silica gel (mobile phase gradient cyclohexane/dichloromethane 50:1 to 5:1). This gave, in two batches, in total 5.73 g (53.6% of theory) of the target compound.MS (DCI): m/z=308/310 (M+NH4)+.GC-MS (Method 1): Rt=4.82 min; m/z=234 (M-C4H8)+.1H-NMR (400 MHz, DMSO-d6): delta=4.29 (q, 1H), 1.78-1.71 (m, 2H), 1.67 (d, 3H), 1.65-1.43 (m, 4H), 1.39 (s, 9H), 0.98 (m, 2H), 0.67 (m, 2H).

The synthetic route of 87661-20-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/28971; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics