Methanol → (2S,4S)-4-methoxypyrrolidine-2-carboxylic acid

Participants

Reaction Steps

A mixture of 6.8 g. of N-carbobenzyloxy-cis-4-methoxy-L-proline, 210 ml. of 2:1 methanol and water, and 2.3 g. of 5% Pd-C is placed on a hydrogenator at 3 atmospheres of hydrogen for four hours. The mixture is filtered to remove the catalyst and the filtrate evaporated to give 3.15 g. of a grayish solid; m.p. 218°-220° (dec.). A sample is crystallized from methanol-ether to yield colorless cis-4-methoxy-L-proline, m.p. 224°-226° (dec.), [α]D25 -42° (c, 1% in methanol).

Provenance & Evidence