Nitrogen → cis-1,1-Dimethylethyl [((3rs,5rs)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-3-piperidinyl)methyl]carbamate

Participants

Reaction Steps

To cis-phenylmethyl (3RS,5RS)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-5-[({[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate (550 mg; 1.1 mmol) in EtOH (50 ml) was added Pd/C (150 mg; 10%). The reaction was hydrogenated on a Parr apparatus at 40 psi of H2 for 1.5 hours. The hydrogen was displaced with N2 and the solution was filtered through a pad of Celite® to remove the catalyst which was washed with additional EtOH (50 ml). The filtrate was then concentrated under reduced pressure to give the desired compound (390 mg; 100%) as a pale yellow oil which was used without further purification.

Provenance & Evidence