(2S)-1-(tert-Butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid → Tert-butyl 2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-tert-butoxycarbonyl-2-methylproline (1.10 g, 4.80 mmol) in THF (20 mL) was added dropwise BH3-SMe2 (0.546 mL, 5.76 mmol) at room temp. After the resulting mixture was stirred for 6 hr at 80° C., the mixture was evaporated in vacuo. The residue was diluted with MeOH, washed with n-hexane (3×), and evaporated in vacuo to afford 0.648 g (60%) N-tert-butoxycarbonyl-2-hydroxymethyl-2-methylpyrrolidine as a yellow syrup. 1H-NMR (CDCl3) δ 1.47 (s, 9H), 1.76–2.05 (m, 4H), 3.28–3.48 (m, 2H), 3.66 (m, 2H, d).

Provenance & Evidence