tert-Butyl ((1-benzylpyrrolidin-3-yl)methyl)carbamate → tert-butyl N-((pyrrolidin-3-yl)methyl)carbamate

Participants

Reaction Steps

1-Benzyl-3-(RS)-(N-tert-butoxycarbonylaminomethyl)pyrrolidine (22.2 g, 0.76 mol) was dissolved in a mixture of methanol and acetic acid (1:1, 100 mL) and added to a Parr flask charged with palladium on carbon (10%, 4 g) suspended in methanol and acetic acid (1:1, 100 mL). The flask was transferred to the Parr reduction apparatus and the suspension shaken under an atmosphere of hydrogen at 60 psi for 2 days. The reaction mixture was filtered through a celite plug, eluting with a mixture of methanol/methylene chloride. The solvent was concentrated and the residue co-evaporated with toluene to afford 3-(RS)-(N-tert-butoxycarbonylaminomethyl)pyrrolidine as a colorless oil which was used directly.

Provenance & Evidence