Chloroform → (3R,5S)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-3-ol

Participants

Reaction Steps

A slurry of 10% Pd/C (190 mg) in ethyl acetate (20 mL) was added to a solution of TBDMS ether (48) (1.90 g, 5.19 mmol) in ethanol (100 mL). The reaction mixture was hydrogenated (Parr apparatus) for 16 h. The catalyst was removed by vacuum filtration through Celite and excess solvent was evaporated under reduced pressure to give a yellow oil in quantitative yield (1.20 g, 100%). [α]22D=+35.6° (c 0.042, CHCl3). 1H NMR (CDCl3): δ-(0.07-0.08) (m, 6H, H1′, H2′), 0.82 (s, 9H, H3′, H4′, H5′), 1.68-1.73 (m, 2H, H1,), 2.99-3.11 (m, 2H, H11), 3.47-3.50 (m, 3H, H11a, H3), 4.09 (bs, 1H, NH or OH), 4.32 (bs, 1H, NH or OH). 13C NMR (CDCl3): δ−5.4 (C3′, C5′, C6′), 18.1 (C4′), 25.8 (C1′, C2′), 37.4 (C1), 54.6 (C11), 58.1 (C2), 64.6 (C3), 72.2 (C11a). IR (thin film): ν=3330 (OH), 2928, 2857, 1557, 1421, 1331 (C—CH3), 1249 (CH3—Si), 1204 (t-Bu), 1191 (t-Bu), 1100 (Si—O), 1073, 993, 713 cm−1. MS (CI) m/e (relative intensity): 232 (M+., 100), 230 (13), 174 (5), 133 (6), 86 (6).

Provenance & Evidence