Methanol → (1R,2S)-2-(Methoxycarbonyl)cyclohexane-1-carboxylic acid

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Reaction Steps

A mixture of 2 g (0.013 mol) of cis-1,2-cyclohexane-dicarboxylic anhydride in 15 mL of methanol was refluxed for 5 hr, then evaporated to dryness under reduced pressure to give 2.41 g (100% yield) of cis-2-methoxycarbonylcyclohexane-carboxylic acid. When this was substituted for 3 in Example 1, the identical process afforded the title compound, melting at 140°-144° C., in 36% yield; Rf (D)=0.53, 0.47.

Provenance & Evidence