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

Participants

Reaction Conditions

Reaction Steps

β-[[(1,1-dimethylethoxy)carbonyl]amino]-α-hydroxycyclohexanebutanoic acid, 1-methylethyl ester (mixture of [R-(R*,S*)] and [S-(R*,R*)]isomers) (Example F), 3.4 g (10 mmol), is dissolved in methylene chloride, cooled to 0° C. and hydrochloric acid gas is bubbled in for five minutes every 15 minutes for two hours. The solution is diluted with ethyl acetate (50 ml) washed with saturated sodium bicarbonate solution (100 ml) and then with saturated brine solution (100 ml). The organics are separated, dried over magnesium sulfate and evaporated to dryness in vacuo to give 1.75 g (73%) of the title compound as an oil.

Provenance & Evidence