Reaction #10470

Reaction equation

racemic 3-[2-(4-methylphenyl)-5-methyloxazol-4-yl-methoxy]cyclohexan-1-ol

→

(1S,3R)-3-[2-(4-methylphenyl)-5-methyloxazol-4-ylmethoxy]cyclohexan-1-ol

Yield 52.8%

Solvents

vinyl acetate

Conditions

Workup

1. 1
   Filtrationthe enzyme was filtered off
2. 2
   Concentrationthe solution concentrated under reduced pressure, crude product

Procedure

16.3 g of the racemic 3-[2-(4-methylphenyl)-5-methyloxazol-4-yl-methoxy]cyclohexan-1-ol were dissolved in 100 ml of vinyl acetate, admixed with 1.9 g of Chirazyme L-2, lyo., and stirred at 20–23° C. After about 30 minutes, the enzyme was filtered off and the solution concentrated under reduced pressure, crude product: 16.6 g. After chromatography on silica gel (10:1–0:1 n-heptane/ethyl acetate), 8.6 g of (1S,3R)-3-[2-(4-methylphenyl)-5-methyloxazol-4-ylmethoxy]cyclohexan-1-ol and 6.8 g of the (1R,3S)-acetate are obtained.

Source