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Preparation method of trans-1,2-cyclohexanedimethanol

A compound and selected technology, applied in the field of pharmaceutical intermediates, can solve the problems of low resolution yield, low photochemical purity, a large amount of waste liquid, etc., and achieve the effect of improving yield and photochemical purity

Pending Publication Date: 2020-04-28
JIANGSU VCARE PHARMATECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In order to solve the problems of low resolution yield, low photochemical purity and large amount of waste liquid in the process of preparing (1R,2R)-1,2-cyclohexanedimethanol in the prior art, the present invention provides a A technical route including bioenzyme chiral catalysis technology, compared with the existing technical route, this method has high product yield, optical selectivity and environmental friendliness

Method used

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  • Preparation method of trans-1,2-cyclohexanedimethanol
  • Preparation method of trans-1,2-cyclohexanedimethanol
  • Preparation method of trans-1,2-cyclohexanedimethanol

Examples

Experimental program
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Effect test

Embodiment 1

[0057]

[0058] Preheat and melt cis-hexahydrophthalic anhydride (220Kg, 1.427Kmol), then dissolve and dilute it with methanol (522Kg) and add it to the reaction kettle, slowly add concentrated sulfuric acid (28Kg, 0.285Kmol) dropwise, and heat to 65-70°C after dropping Reflux for 12 hours, add sodium bicarbonate to adjust the pH to 7-8, collect the filtrate by filtration, add water (220Kg), then extract with dichloromethane (874Kg), concentrate under reduced pressure to dryness to obtain the oil cyclohexane-1, Dimethyl 2-dicarboxylate III-a 280Kg, yield 98%.

Embodiment 2

[0060]

[0061]Add cis-hexahydrophthalic anhydride (500g, 3.244mol) into the reaction flask, add ethanol (1.5L) to dissolve and disperse, slowly add concentrated sulfuric acid (64g, 0.65mol) dropwise, and heat to 75-80°C under reflux for reaction 16 hours, add sodium bicarbonate to adjust the pH to 7-8, collect the filtrate by filtration, add water (500mL), extract with dichloromethane (1.5L), and concentrate under reduced pressure to dryness to obtain oil cyclohexane-1,2- Diethyl dicarboxylate III-b 688g, yield 93%.

Embodiment 3

[0063]

[0064] Add cis-hexahydrophthalic anhydride (100g, 0.648mol) into the reaction flask, add isopropanol (300mL) to dissolve and disperse, slowly add concentrated sulfuric acid (12.7g, 0.13mol) dropwise, and heat to reflux at 70-85°C after dropping React for 24 hours, add sodium bicarbonate to adjust the pH to 7-8, collect the filtrate by filtration, add water (200mL), then extract with dichloromethane (600mL), concentrate under reduced pressure to dryness to obtain oily cyclohexane-1,2 -Diisopropyl dicarboxylate III-c 134g, yield 81%.

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Abstract

The invention relates to a preparation method of trans-1,2-cyclohexanedimethanol. The trans-1,2-cyclohexanedimethanol is obtained through steps of esterification, enzymatic hydrolysis, hydrolysis, esterification and reduction, wherein in the step of enzymatic hydrolysis, escherichia coli hydrolase or saccharomyces cerevisiae hydrolase is used. The ee value and the yield of an obtained optically-pure compound as shown in a formula IV are far higher than those of a compound obtained by a chemical resolution method, besides, massive waste liquid cannot be produced, and environmental protection isfacilitated.

Description

technical field [0001] The invention relates to the field of pharmaceutical intermediates, in particular to a preparation method of (1R,2R)-1,2-cyclohexanedimethanol. Background technique [0002] Lurasidone hydrochloride is an atypical antipsychotic that acts on serotonin receptors and dopamine D 2 The receptors have a high affinity, and it has a significant effect on the positive and negative symptoms of mental patients, and the extrapyramidal symptoms (EPS) of this product are very low, and it has a very good effect on the treatment of mental patients with cognitive dysfunction. [0003] (1R,2R)-1,2-Cyclohexanedimethanol is a key intermediate for the synthesis of lurasidone hydrochloride, and its structure is as follows: [0004] [0005] JP2004224764A discloses its preparation method: using cis-hexahydrophthalic anhydride as a raw material, the specific carboxylic acid is obtained through acidification and hydrolysis, and the specific carboxylic acid is resolved by a...

Claims

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Application Information

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IPC IPC(8): C12P7/62C07C29/147C07C31/27
CPCC12P7/62C07C67/08C07C51/09C07C29/147C07C2601/14C07B2200/07C07C69/75C07C61/09C07C31/276Y02P20/55
Inventor 周西朋陈涛秦小飞阳军龚彦春刘永强
Owner JIANGSU VCARE PHARMATECH
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