beta-[[(1,1-Dimethylethoxy)carbonyl]amino]-alpha-hydroxybenzenebutanoic acid, 1-methylethyl ester → beta-[[(1,1-Dimethylethoxy)carbonyl]amino]-alpha-hydroxycyclohexanebutanoic acid, 1-methylethyl ester

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Reaction Steps

To β-[[(1,1-dimethylethoxy)carbonyl]amino]-α-hydroxybenzenebutanoic acid, 1-methylethyl ester (mixture of R-(R*,S*)] and [S-(R*,R*)]isomers) (Example E), 4.2 g (12.4 mmol), in isopropanol (100 ml) is added 10% rhodium on carbon, 1.0 g, and the mixture is stirred under a hydrogen atmosphere for 16 hours. The solution is filtered and evaporated in vacuo to give a 3.6 g (85%) of the title compound as a tan oil.

Provenance & Evidence