反应详情

To a stirred solution of N-Boc-5-(R)-phenyl-(2S)-proline (1.14 g, 3.91 mmol) in THF (20 ml) was added 10M-BH3.Me2S (780 ml, 7.82 mmol) at rt, and the resulting mixture was heated under reflux for 30 min. The mixture was poured into aq. 1N-HCl and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, then concentrated in vacuo. The residue was chromatographed on silica gel with CHCl3—MeOH (10:1) as eluent to give N-Boc-2-(S)-hydroxymethyl-5-(R)-phenylpyrrolidine (1.11 g, quant.) as a colorless oil: 1H-NMR (CDCl3) δ1.19 (brs, 9 H), 1.65 (brs, 1 H), 1.83-1.90 (m, 1 H), 1.98-2.06 (m, 1 H), 2.22-2.31 (m, 1 H), 3.75-3.86 (m, 2 H), 4.16-4.19 (m, 1 H), 4.83 (t, J=6.8 Hz, 1 H), 4.89 (brs, 1 H), 7.19-7.31 (m, 5 H); MS (ESI) m/z, 2.78 (M++H).

1. temperatureunder reflux for 30 min
2. extractionextracted with EtOAc
3. dry with materialThe organic layer was dried over anhydrous Na2SO4
4. concentrationconcentrated in vacuo
5. customThe residue was chromatographed on silica gel with CHCl3—MeOH (10:1) as eluent