Preparation method of 1S,4R-1-methyl-4-(1-methylvinyl)-2-cyclohexene-1-ol

Abstract

The invention relates to a novel synthesis route of 1S,4R-1-methyl-4-(1-methylvinyl)-2-cyclohexene-1-ol. According to the preparation method, limonene is taken as the raw material, 1S,4R-1-methyl-4-(1-methylvinyl)-2-cyclohexene-1-ol is synthesized after four steps: epoxidation reactions, addition reactions, oxidation reactions, and elimination reactions, and the yield is high. The provided 1S,4R-1-methyl-4-(1-methylvinyl)-2-cyclohexene-1-ol preparation method has the advantages of high yield, high chiral purity product, low cost, environmental friendliness, and easy operation, and is suitablefor industrialization.

Description

technical field [0001] The invention relates to the field of medicines, in particular to a preparation method of 1S,4R-1-methyl-4-(1-methylvinyl)-2-cyclohexen-1-ol. Background technique [0002] With the development of science and technology, people's living standards are getting better and better, but with the increasing number of cancer diagnoses every year, the research and development of anticancer drugs is an urgent matter, and 1S,4R-1-methyl- 4-(1-methylvinyl)-2-cyclohexen-1-ol is an effective intermediate of anticancer drugs, so its large-scale and efficient synthesis is also a problem that we need to solve. [0003] The currently reported method is as follows: [0004] US2014329895 discloses a preparation method of (1S,4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexen-1-ol, as attached figure 2 As shown, although this scheme can also stereoselectively generate (1S, 4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexen-1-ol, it has many processing steps, The cost is high and the y...

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Problems solved by technology

[0004] US2014329895 discloses a preparation method of (1S,4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexen-1-ol, as attached figure 2 As shown, although this scheme can also stereoselectively generate (1S, 4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexen-1-ol, it has many processing steps, The cost is high and the yield is low, so it is not suitable for industrial production. At the same time, compared with the predecessor Reddy B.M, the expensive oxide (zirconyl sulfate) is used as a catalyst to selectively carry out the ring-opening reaction, while Peddinti R.K. uses more catalytic equivalents (10mol% ) and unstable chloride (antimony chloride) to catalyze the reaction, the best Saidi M.R. uses heteropolyacid (phosphotungstic acid) as catalyst, which will also catalyze the ring opening of epoxide

But to sum up their research, catalysts are required and cannot be recycled, which undoubtedly brings cost consumption to industrial production

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