反应详情

To a stirred solution of 1-(tert-butoxycarbonyl)4-(2,4-difluorophenoxy)pyrrolidine-2-carboxylic acid (2.55 g, 7.43 mmol) in THF (50 ml) was added BH3.DMS (452 ul, 7.43 mmol). The mixture was heated at reflux overnight. After cooling to room temperature, the mixture was concentrated in vacuo and quenced by the addition of H2O (100 ml). The mixture was extracted with CHCl3 (2×200 ml), dried over MgSO4, and evaporated. The residue was chromatographed on silica gel with CHCl3-EtOAc (4:1) as eluent to give 1-(tert-butoxycarbonyl)-4-(2,4-difluorophenoxy)-2-pyrrolidinylmethanol (1.76 g, 72%) as a colorless oil. 1H-NMR (CDCl3) δ 1.45 (s, 9 H), 2.28–2.36 (m, 2 H), 3.58–4.99 (series of m, 8 H), 6.74–6.90 (m, 3 H).

1. temperatureThe mixture was heated
2. temperatureat reflux overnight
3. concentrationthe mixture was concentrated in vacuo
4. additionquenced by the addition of H2O (100 ml)
5. extractionThe mixture was extracted with CHCl3 (2×200 ml)
6. dry with materialdried over MgSO4
7. customevaporated
8. customThe residue was chromatographed on silica gel with CHCl3-EtOAc (4:1) as eluent