HCID 11000775, compound → tert-Butyl ((3S,5S)-5-methylpyrrolidin-3-yl)carbamate

Participants

Reaction Steps

A 4.500 g (15.50 mmol) sample of (2S,4S)-4-t-butoxycarbonylamino-2-methyl-1-N-benzylpyrrolidine, from Example 2 above, was dissolved in 150 mL of methanol, 0.90 g of 10% Pd/C was added and the mixture shaken under 4 atm of hydrogen at room temperature for 13 hours. The mixture was concentrated, the catalyst was removed by filtration, and the solvent removed to afford 3.081 g of the title compound as a white solid. MS M/Z: 201 (M+H). NMR (CDCl3) δ: 1.15 (d, 3H, J=6 Hz), 1.44 (s, (1H), 1.54-1.63 (m, 2H), 1.75 (m, 1H), 2.64 (dd, 1H, J=5, J=12 Hz), 3.26 (m, 1H), 3.38 (dd, 1H, J=7, J=12 Hz), 4.12 (br, 1H), 4.63 (br, 1H). IR (KBr): 1685 cm-1.

Provenance & Evidence