HCID 12772862, compound → HCID 11126946, compound

Participants

Reaction Steps

500 ml of toluene containing 100 g of methyl 2,3-epoxy-3-cyclohexylpropionate, was added to 500 ml of a 1M tris-HCl buffer solution (pH 8.0) containing lipase (derived from hog pancreas, manufactured by Wako Pure Chemical Industries, Ltd.) in a concentration of 5 g/l, and asymmetric hydrolysis reaction was carried out at 30° C. for 48 hours at a stirring speed of 600 rpm. After the reaction, the toluene phase was separated and concentrated under reduced pressure to obtain 25.2 g of a crude product of methyl (2S,3R)-2,3-epoxy-3-cyclohexylpropionate as a colorless oil substance. By purification by silica gel chromatography (hexane/ethyl acetate=9/1 (v/v)), 23.0 g of methyl (2S,3R)-2,3-epoxy-3-cyclohexylpropionate was obtained (98.6% ee [α]D20=+32.6 (c 1.18, CHCl3)).

Provenance & Evidence