Borane;tetrahydrofuran → Tert-butyl 4-fluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

To a stirred solution of 1-tert-butoxycarbonyl-4-fluoropyrrolidine-2-carboxylic acid (1.1 g, 4.7 mmol) in THF (10.0 ml) was added BH3.THF (1.0 M solution in THF, 10.0 ml, 10.0 mmol) at 0° C. After stirred at room temperature for 1.0 h. After cooled, the mixture was concentrated in vacuo. Water was added thereto at 0° C., and extracted with EtOAc. The extract was washed with water, then dried over Na2SO4, and concentrated in vacuo to give 1-tert-butoxycarbonyl-4-fluoro-2-pyrrolidinylmethanol (1.0 g, quant) as a a colorless oil. 1H-NMR (CDCl3) δ1.48 (s, 9H), 2.29-2.39 (m, 1H), 3.38-3.59 (m, 2H), 3.74-3.88 (m, 2H), 4.09-4.14 (m, 2H), 4.85 (m, 1H), 5.03 (br s, 1H), 5.16 (br s, 1H).

Provenance & Evidence