Methanol → HCID 53890036, compound

Participants

Reaction Steps

A mixture of 1-[[ethyl[[ethoxy(4-phenylbutyl)phosphinyl]methyl]amino]carbonyl]-L-proline, phenylmethyl ester (800 mg., 1.56 mmole), methanol (50 ml.), and 10% palladium on carbon catalyst (150 mg.) was hydrogenated on the Parr apparatus at 50 psi for 1.5 hours. The catalyst was removed by filtration (Celite bed) and the methanol stripped to give 600 mg. residue. This residue was passed through a pad of silica eluting with dichloromethane/methanol/acetic acid (100/5/5) to remove a polar impurity. After evaporation and azeotropic removal (toluene) of residual acetic acid, 550 mg. of 1-[[ethyl[[ethoxy(4-phenylbutyl)phosphinyl]methyl]amino]carbonyl]-L-proline was obtained as an oil. Tlc (dichloromethane/methanol/acetic acid; 100:5:5) single spot at Rf =0.6.

Provenance & Evidence