Benzyl chloroformate → benzyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

2-Pyrrolidinemethanol (2 g, 20 mmol) was dissolved in CH2Cl2 (25 mL) followed by addition of saturated NaHCO3 (25 mL). To this vigorously stirred mixture was added benzylchloroformate via syringe slowly at 0° C. The reaction mixture was then stirred at room temperature for 4 h. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3×80 mL). The combined organic layer was washed with brine, and dried (Na2SO4). Removal of the solvent provided 4.7 g of the title compound, which was used, directly for next step. 1H NMR (CDCl3): δ 7.50-7.30 (aromatic Hs, 5H); 5.17 (s, 2H); 4.04 (brs, 1H); 3.66 (m, 2H); 3.57 (m, 1H); 3.42 (m, 1H); 2.04 (m, 1H); 1.89 (m, 1H); 1.83 (m, 1H); 1.62 (m, 1H).

Provenance & Evidence