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

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Reaction Steps

8 g of methyl 2-(cis-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate are dissolved in 100 ml of vinyl acetate, and 1 g of Candida antartika lipase B is added. The mixture is stirred at room temperature for seven hours and the enzyme is then 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). This gives 3.9 g of the alcohol methyl 2-((1R,3S)-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate as a colorless oil. C16H22O4 (278.35), MS(ESI): 279 (M+H+), ee=98% (Chiralpak AD/2 250×4.6; n-heptane:ethanol:methanol=25:1:0.5+0.1% trifluoroacetic acid, Rt=8.9 min; retention time of the enantiomer: Rt=9.9 min).

Provenance & Evidence