Category: 3618-04-0

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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C9H16O3

A 250-mE 3-necked round-bottom flask fitted with a magnetic stir bar and thermometer was charged with ethyl 4-hydroxycyclohexane-i -carboxylate (1.5 g, 8.71 mmol), tnethylamine (2.64 g, 26.09 mmol) and dichloromethane (50 mE). To the reaction was added methanesulfonyl chloride (1.49 g, 13.01 mmol) added dropwise with stirring at 00 C. The resulting solution was stirred for 2 h at 25° C. The resulting solution was diluted with water (20 mE) and the product was extracted with dichloromethane (3×20 mE). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (1:5, v/v) to afford ethyl 4-(methane- sulfonyloxy) cyclohexane- 1 -carboxylate as a light yellow oil (1.2 g, 55percent). ECMS: (ESI) mlz 251 [M+H], 155 [M-OMs].

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; Forma Therapeutics, Inc.; Ioannidis, Stephanos; Talbot, Adam Charles; Follows, Bruce; Buckmelter, Alexandre Joseph; Wang, Minghua; Campbell, Ann-Marie; Schmidt, Darby Rye; Guerin, David Joseph; Caravella, Justin A.; Diebold, R. Bruce; Ericsson, Anna; Lancia, JR., David; (225 pag.)US2016/185785; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 3618-04-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 3618-04-0 as follows.

Chloro(1 ,1-dimethylethyl)dimethylsilane (115g; 0.76mol) was added in portions over 1 hour to a solution of ethyl 4-hydroxycyclohexanecarboxylate (118g; 0.68mol), imidazole(103g; 1.52mol) and dimethylformamide (400ml) stirred under an atmosphere of argon. A small exotherm was observed resulting in the reaction mixture temperature increasing to~40C. The mixture was stirred at room temperature overnight then poured into 10% citric acid solution (2L) and extracted with diethyl ether (2 x 800ml). The ether extracts were washed with water, brine and then dried (Na2SO4) and the solvent was removed to give the title compound as a oil (198.4g) 1H NMR delta (CDCI3, 400 MHz): 0.01 (6H, m), 0.85 (9H, s), 1.2 (3H, m), 1.3-1.5 (2H, m), 1.6 (2H, m), 1.85-2 (3H, m), 2.15-2.3 (1 H, m) 3.5 (0.4H, m) 3.86 (1 H, m) 4.1 (1 H, m).

According to the analysis of related databases, 3618-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/107565; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 3618-04-0, A common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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 oxalyl chloride (6 mL, 68.8 mmol) in DCM (100 mL) at -78° C. was added dropwise a solution of DMSO (6.4 mL, 90 mmol) in DCM (20 mL). The mixture was stirred at this temperature for 15 min before the dropwise addition of a solution of ethyl 4-hydroxycyclohexane carboxylate (4.8 mL, 30 mmol) in DCM (20 mL). The mixture was stirred at -78° C. for 3 h before addition of TEA (29.3 mL, 210 mmol) in DCM (20 mL). The mixture was then gradually warmed to rt, washed with a sat. aq. NH4Cl solution and brine, dried over MgSO4 and concentrated. The residue was purified by chromatography over SiO2 (Hex/EA 1:1) to give the title ketone (4.6 g, 90percent yield) as a colourless oil. 1H NMR (CDCl3) delta: 4.19 (q, J=7.1 Hz, 2H); 2.80-2.70 (m, 1H); 2.55-2.45 (m, 2H); 2.40-2.30 (m, 2H); 2.25-2.10 (m, 2H); 2.05-2.00 (m, 2H); 1.29 (t, J=7.1 Hz, 3H).

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; US2009/105232; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 3618-04-0, 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. 3618-04-0 name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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.

tert-Butyldimethylsilyl chloride (26.3 g, 174 mmol) was added to a solution of ethyl 4- hydroxycyclohexanecarboxylate (25.0 g, 145 mmol, mixture of cis-/trans-isomers, Gas No 17159-80-7) and imidazole (24.7 g, 363 mmol) in DMF (36 ml) and the mixture was stirred overnight at room temperature. For work-up, water was added and the mixture was extracted with tert-butyl methyl ether (3x). The combined organic phases were washed with brine, filtered through a silicone filter and concentrated under reduced pressure to yield ethyl 4-{[tert- butyl(dimethyl)silyl]oxy}cyclohexanecarboxylate (43.1 g, 104% yield) which was used in the next step without further purification.1HNMR (400 MHz, DMSO-d6, mixture of isomers): 6 [ppm] = 4.10-3.99 (m, 2H), 3.93-3.86 (m,0.7H), 3.63-3.51 (m, 0.3H), 2.39-2.28 (m, 0.8H), 2.27-2.14 (m, 0.3H), 1.91-1.21 (m, 8H), 1.20-1.13 (m, 3H), 0.89-0.79 (m, 9H), 0.08-0.00 (m, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, trans-Ethyl 4-hydroxycyclohexanecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; WAGNER, Sarah; SUeLZLE, Detlev; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; (232 pag.)WO2018/78009; (2018); 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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: trans-Ethyl 4-hydroxycyclohexanecarboxylate

4-Toluenesulfonyl chloride (18.29 g, 96 mmol) was added in several portions to a solution of ethyl 4-hydroxycyclohexanecarboxylate (ca. 1:1 mixture of cis and trans ring isomers) (29.5 g, 90 mmol) in pyridine (100 mL) in an ice-water bath, and the mixture stirred, allowing to warm to RT. After the solid had dissolved, the mixture was allowed to stand. After 24 h, the mixture was concentrated and the residue partitioned between water and EtOAc (100 mL each). The organic phase was dried and concentrated to give ethyl 4-(tosyloxy)cyclohexanecarboxylate (ca. 1:1 mixture of cis and trans ring isomers) (crude, 29.5 g) as a colourless oil which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) delta ppm 1.20-1.30 (m, 3H) 1.44-2.08 (m, 8H) 2.21-2.43 (m, 1H) 2.48 (s, 3H) 4.08-4.20 (m, 2H) 4.40-4.50 and 4.70-4.78 (both m, total 1H) 7.28-7.40 (m, 2H) 7.78-7.86 (m, 2H)

According to the analysis of related databases, 3618-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; BUFFHAM, William; CANNING, Hannah; DAVENPORT, Richard; FARNABY, William; MACK, Stephen; PARMAR, Alka; WRIGHT, Susanne; US2015/57298; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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 3618-04-0, HPLC of Formula: C9H16O3

tert-Butyldimethylsilyl chloride (26.3 g, hydroxycyclohexanecarboxylate (25.0 g, 171 59-80-7) and imidazole (24.7 g, 363174 mmol) was added to a solution of ethyl 4-145 mmol, mixture of cis-/trans-isomers, Gas Nommol) in N,N-dimethylformamide (36 ml) and the mixture was stirred over night at room temperature. For work-up, water was added and the mixture was extracted with tert-butyl methyl ether (3x). The combined organic phases were washed with brine, filtrated through a silicone filter and concentrated under reduced pressure to yield ethyl 4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexanecarboxylate (43.1 g, 104% yield) which was used in the next step without further purification. 1HNMR (400 MHz, DMSO-d6, mixture of isomers): 6 [ppm] = 4.10-3.99 (m, 2H), 3.93-3.86 (m, 0.7H), 3.63-3.51 (m, 0.3H), 2.39-2.28 (m, 0.8H), 2.27-2.14 (m, 0.3H), 1.91-1.21 (m, 8H), 1.20-1.13 (m, 3H), 0.89-0.79 (m, 9H), 0.08-0.00 (m, 6H).

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, trans-Ethyl 4-hydroxycyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 3618-04-0,Some common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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.

tert-Butyldimethylsilyl chloride (8.8 g, 58 mmol) was added to a solution of ethyl 4- hydroxycyclohexanecarboxylate (10 g, 58 mmol) and imidazole (4.3 g, 64 mmol) in DCM (300 ml), and the mixture was stirred overnight at 20 0C. After washing with water (2 X 100 ml), the organic phase was dried (MgSO4) and evaporated to dryness. The residue was dissolved in dry THF (300 ml) and cooled to -10 0C. Dibal-H (1.0 M in toluene, 174 ml, 174 mmol) was added dropwise over a period of 60 min, while the temperature was kept at – 100C. After stirring for 2 hrs the reaction was quenched by slow addition of a saturated ammonium chloride solution (30 ml). The resulting suspension was filtered, and the filtrate was concentrated in vacuo to give 13 g of the title compound as a mixture of two isomers. LC-MS {m/z) : 245 (M + l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route trans-Ethyl 4-hydroxycyclohexanecarboxylate, its application will become more common.

Reference:
Patent; TRANSTECH PHARMA; WO2008/101914; (2008); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 3618-04-0, The chemical industry reduces the impact on the environment during synthesis 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, I believe this compound will play a more active role in future production and life.

EXAMPLE 5 5-Butyl-9-[1-(4,6-dimethyl-pyrimidine-5-carbonyl)-4-methyl-piperidin-4-yl]-3-(trans-4-hydroxy-cyclohexylmethyl)-1-oxa-3,9-diaza-spiro[5.5]undecan-2-one (I-4) 4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester (38)-To a solution of 4-oxy-cyclohexanecarboxylic acid ethyl ester (CASRN 17159-80-7, 1.7 g, 0.01 mol) in DMF (14 mL) was added DMAP (58 mg, 0.47 mmol), TEA (1.54 mL) and tert-butyl-dimethylsilyl chloride (1.65 g, 0.011 mol). The reaction mixture was stirred at RT for 18 h, poured into ice (10 g), extracted with EtOAc (3*50 mL). The organic extracts were dried (MgSO4) filtered and concentrated. The residue was purified by SiO2 chromatography eluding with EtOAc/hexane (1:20) to afford 2.25 g (79%) of 4-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester (38) as colorless oil.

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, trans-Ethyl 4-hydroxycyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Rotstein, David Mark; Melville, Chris Richard; US2008/249087; (2008); 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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H16O3

INTERMEDIATE B-33Step 1 : ethyl 4-(5-bromopyridin-2-yloxy)cycIohexanecarboxylate (B-31)To a solution of 5-bromo-2-hydroxypyridine B-30 (1.0 g, 5.75 mmol) and ethyl 4- hydroxycyclohexanecarboxylate (990 mg, 5.75 mmol) in THF (50 mL) was added PPh3 (2.4 g, 9.150 mmol) and DIAD (1.8 mL, 9.14 mmol). The reaction mixture was stirred at RT for 17 h. The solution was then concentrated and purified by ISCO to yield ethyl 4-(5- bromopyridin-2-yloxy)cyclohexanecarboxylate as a colorless oil (1.16 g, 62percent yield, 3:2 trans:cis ratio).

According to the analysis of related databases, 3618-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; TING, Pauline, C.; LEE, Joe, F.; ASLANIAN, Robert, G.; WO2011/31628; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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. Recommanded Product: trans-Ethyl 4-hydroxycyclohexanecarboxylate

VII) Synthesis of CP30450-3; Ethyl 4-[(/erf-butyldimethylsilyl)oxy]cyclohexanecarboxylate (55); Following protocols reported by Wild,10 a solution of Ethyl 4- hydroxycylohexanecarboxylate (54) (1.0 mL, 6.20 mmol) in DMF (3.0 mL) was treated with imidazole (929 mg, 13.6 mmol) and tert-butyldimethylsilyl chloride (1.22 g, 8.09 mmol) and the resulting mixture stirred magnetically at 18 °C under a nitrogen atmosphere for 20 h. The reaction mixture was then treated with Et2O (50 mL), washed with HCl (1 x 5 mL of a 1 M aqueous solution), then dried (MgSO4), filtered and concentrated under reduced pressure. The ensuing residue was subjected to flash chromatography (hexane- 1:49 v/v ethyl acetate/hexane gradient elution) to afford a ca. 1:1 mixture of the cis- and troens-isomeric forms of the title compound 55 (1.78 g, quant.) as a colourless oil, Rf 0.7 in 3:7 v/v ethyl acetate/hexane.1H NMR (300 MHz) delta 4.12 and 4.11 (2 x q, J 7.1 and 7.1 Hz, 2 x 2H), 3.89 and 3.56 (2 x m, 2 x IH), 2.33-2.16 (complex m, 2 x IH), 1.98-1.87 (complex m, 2 x 2H), 1.68-1.22 (complex m, 2 x 6H), 1.25 and 1.24 (2 x t, J 7.1 and 7.1 Hz, 2 x 3H), 0.88 and 0.87(8) (2 x s, 2 x 9H), 0.05 and 0.03 (2 x s, 2 x 6H).13C NMR (75 MHz) delta 175.8 and 175.7 (2 x C), 70.5 and 66.6 (2 x CH), 60.1 and 60.0 (2 x CH2), 42.2 and 42.0 (2 x CH), 34.8 and 32.8 (4 x CH2), 27.2 and 23.4 (4 x CH2), 25.8 and 25.7(7) (6 x CH3), 18.2 and 18.1 (2 x C), 14.2 (2 x CH3), -4.7 and -4.9 (4 x CH3). IR vmax/cm”1 2934, 2858, 1734, 1463, 1252, 1096, 1049, 835, 774.Mass Spectrum (EI) m/z 229 [(M-C4Hg)+’, 92], 57 (100).HRMS found: (M-C4H9)+\ 229.1256. C15H30O3Si requires (M-C4Hg)+’, 229.1260.

The synthetic route of trans-Ethyl 4-hydroxycyclohexanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CRYPTOPHARMA PTY LTD; WO2008/124878; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics