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Synthetic method of 3,3-dimethylcyclohexanone

A technology of dimethylcyclohexanone and a synthesis method, applied in the field of drug synthesis, can solve the problems of serious corrosion of equipment, difficult purification and the like, and achieve the effects of low cost, easy scale-up production and alleviation of purification difficulty.

Inactive Publication Date: 2019-06-04
SUZHOU PENGXU PHARM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that it uses a strong acidic reagent, which severely corrodes the equipment; and there is an over-reduced by-product 3,3-dimethylcyclohexanol in the reaction system, which is difficult to purify

Method used

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  • Synthetic method of 3,3-dimethylcyclohexanone
  • Synthetic method of 3,3-dimethylcyclohexanone
  • Synthetic method of 3,3-dimethylcyclohexanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 Preparation of Compounds 1 and 3

[0028] Add 10.0 g of compound 2 to 100 mL of isopropanol and 0.5 g of 5% Pd / C. React at 65°C for 48 hours under 2 MPa hydrogen pressure. The Pd / C was removed by filtration, and the reaction solution was concentrated to obtain a mixture of compound 1 and compound 3 (the ratio on GC was about 17:1), and the subsequent reaction was carried out directly without separation.

Embodiment 2

[0029] Example 2 Preparation of compound 1

[0030] Add 100 mL of dichloromethane and 100 mL of water to the mixture obtained in Example 1 above. Add 14.7 g sodium bromide, 9 g sodium bicarbonate. Stir and cool down to 0~10°C, add 0.2 g TEMPO, and dropwise add 101 g 5% sodium hypochlorite aqueous solution to react. Complete conversion of compound 3 to compound 1 was detected by GC. The crude product of compound 1 was obtained after separation and washing with water, and the GC purity was as high as 95%. Compound 1 (3,3-dimethylcyclohexanone) was obtained after distillation.

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Abstract

The invention relates to the field of drug synthesis, specifically to a synthetic method of 3,3-dimethylcyclohexanone. The synthetic method has mild reaction condition and is easy for amplifying production. Various reagents used in the invention are all easily available in the market, and are low-cost. The by-product 3,3-dimethylcyclohexanol is effectively converted into the product 3,3-dimethylcyclohexanone through an intermediate step of oxidation reaction. The yield is increased, and the purification difficulty is reduced.

Description

technical field [0001] This application relates to the field of drug synthesis, in particular, to a synthesis method of 3,3-dimethylcyclohexanone. Background technique [0002] Venetoclax is an anticancer drug jointly developed by AbbVie and Roche, which was approved by the FDA on April 11, 2016. And 3,3-dimethylcyclohexanone is an important raw material for the synthesis of venetoclax. [0003] So far, there are not many reports about the synthesis of 3,3-dimethylcyclohexanone in domestic and foreign patents. Such as patents CN 105753680, CN 102066290. [0004] Patent CN 105753680 reports the synthesis of 3,3-dimethylcyclohexanone by secondary methylation using cyclohexanone as raw material at 170-200°C, 1-1.4 atmospheric pressure and pH 5-6 . The disadvantage of this method is that the reaction temperature is too high, which is not conducive to large-scale scale-up production; and the risk of incomplete methylation reaction makes it difficult to purify the product. ...

Claims

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Application Information

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IPC IPC(8): C07C45/61C07C45/30C07C49/403C07C29/145C07C35/08
Inventor 李丕旭王鹏刘远华沈炜良
Owner SUZHOU PENGXU PHARM TECH CO LTD
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