Dimethylformamide → tert-butyl N-[(1S,3R)-3-(cyanomethyl)cyclopentyl]carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 8.2 g (0.0222 mol) of N-[t-butoxycarbonyl]-2-(p-toluenesulfonyloxymethyl)cyclopentylamine in DMF (250 mL) was added 3.3 g (0.067 mmol) of NaCN and the suspension was heated at 80° C. for 4 h. The solvent was removed in vacuo at 40° C. and the residue was slurried in brine. The aqueous layer was extracted with ethyl acetate, dried and the solvent was removed in vacuo to yield 5.7 g of the title compound. MS(ES+)m/z=225. (one enantiomer)

Provenance & Evidence