Methyl 2-(cis-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate → methyl 2-((1R,3S)-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate

Participants

Reaction Steps

13.1 g of methyl cis-2-(3-hydroxycyclohexyloxymethyl)-6-methylbenzoate are dissolved in 100 ml of vinyl acetate and 1.6 g of Candida antartika lipase B are added. After eight hours of stirring at room temperature, the enzyme is filtered off and the solvent is removed under reduced pressure. The residue is purified by flash chromatography on silica gel (n-heptane/ethyl acetate=10:1→ethyl acetate). This gives 4.3 g of methyl 2-((1R,3S)-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate as a colorless oil. C16H22O4 (278.35), MS(ESI): 279 (M+H+), ee=99% (Chiralpak AD/2 250×4.6; n-heptane:ethanol:methanol=25:1:0.5+0.1% trifluoroacetic acid, Rt=8.9 min)

Provenance & Evidence