Methanol → (1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanol

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Reaction Steps

24 g of (±)-(3RS,4SR)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanone (compound F1) are dissolved at 60° C. in a mixture consisting of 300 ml of 1,2-dimethoxyethane and 3 ml of methanol and treated portionwise with 1.6 g of sodium borohydride. After 1 h the reaction mixture is cooled to room temperature, 300 ml of water are added and the crude title compound is extracted with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated. The crude title compound is purified by chromatography on silica gel using ethyl acetate/petroleum ether in the ratio 2/1 as eluent. Removal of the solvents of the corresponding eluate fractions yields 11.9 g of the title compound of melting point 119-122° C.

Provenance & Evidence