(2S,4R)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl Ester → 1-tert-butyl 2-methyl (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylate

Participants

Reaction Steps

A mixture of trans-4-azido-N-tert-butoxycarbonyl-L-proline methyl ester (L, 2.00 g) and 10% palladium on activated carbon (601 mg) in methanol (60 mL) was stirred at room temperature for 2.5 hr under hydrogen. The catalysts were removed by filtration and washed with methanol. The combined organic layers were evaporated in vacuo to give the title compound (1.85 g) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 1.41-1.46 (m, 9H), 1.99-2.22 (m, 2H), 2.63 (br s, 2H), 3.13-3.35 (m, 1H), 3.67-3.79 (m, 2H), 3.73 (s, 3H), and 4.36-4.47 (m, 1H).

Provenance & Evidence