N-[1-(S)-ethoxycarbonyl-3-phenyl-3-oxo-propyl]-(S)-alanyl-(S)-proline-t-butylester → N-[1-(S)-ethoxycarbonyl-3-phenyl-3(R)-hydroxypropyl]-(S)-alanyl-(S)-proline-t-butylester

Participants

Reaction Steps

13.4 g (30 mmoles) of N-[1-(S)-ethoxycarbonyl-3-phenyl-3-oxo-propyl]-(S)-alanyl-(S)-proline-t - butylester are dissolved in 120 ml of ethanol and hydrogenated in the presence of 1.5 g of 10% palladium-on-charcoal catalyst at room temperature. After the uptake of the theoretically needed hydrogen (720 ml), the catalyst is filtered off. A mixture of N-[1-(S)-ethoxycarbonyl-3-phenyl-3(S)-hydroxypropyl]-(S)-alanyl-(S)-proline-t-butylester and N-[1-(S)-ethoxycarbonyl-3-phenyl-3(R)-hydroxypropyl]-(S)-alanyl-(S)-proline-t-butylester is obtained.

Provenance & Evidence