Benzyl chloroformate → Benzyl 3-hydroxypyrrolidine-1-carboxylate

Participants

Reaction Steps

A solution of 4.29 g (48.9 mmol) of 3-hydroxypyrrolidine in 30 mL of 2N potassium hydroxide was cooled to 0° C. and 10.2 mL of benzyl chloroformate were added with stirring. The reaction was stirred for four hours at 0° C. and then extracted with ethyl acetate (3×100 mL). The extracts were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated in vacua. The residue was chromatographed on silica gel with 70/30 hexanes/ethyl acetate. The correct fractions were combined and concentrated in vacuo to give 8.87 g (81%) of benzyl 3-hydroxypyrrolidine-1-carboxylate as a viscous clear oil. Rf=0.11 in 50/50 hexanes/ethyl acetate Mass Spectrum (FD+): M+221; IR (CHCl3, cm-1): 913, 977, 993, 1100, 1117, 1175, 1236, 1360, 1427, 1454, 1498, 1694, 2884, 2954, 3013, 3020, 3436 (broad), 3610; UV (C2H5OH) λmax =205 (ε=9112), 264 (ε=142); 1H NMR (300 MHz, CDC13) δ: 1.91-2.05 (m-, 2H); 3.00 (broad s, 1H); 3.39-3.61 (m, 4H); 4.41 (s, 1H); 5.12 (s, 2H); 7.30-7.43 (m, 5H).

Provenance & Evidence