Dimethyl Sulfide → HCID 59838273, compound

Temperature

50 °C

To a stirred solution of (2S, 4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylcarboxylic acid (2.39 g, 7.76 mmol) in THF (50 ml) was added BH3.DMS (1.55 ml, 15.5 mmol) at 0° C. After 10 min. stirring at the same temperature, the mixture was allowed to room temperature and then heated at 50° C. for 2 h. After cooling to room temperature, the mixture was concentrated in vacuo and quenched by the addition of water at 0° C. The mixture was extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and evaporated. The residue was chromatographed on silica gel [60 g, CHCl3/MeOH (50/1)] to give (2S, 4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylmethanol (2.83 g, 100%) as a colorless oil. 1H-NMR (CDCl3) δ 1.47 (s, 9H), 1.95 (br, 1H), 2.36 (m, 1H), 3.56–3.74 (m, 3H), 3.89–4.52 (m, 3H), 4.85 (br, 1H), 6.84 (dd, J=8.8, 1.2 Hz, 2H), 6.97 (t, J=7.2 Hz, 1H), 7.29 (t, 2H, J=7.8 Hz).

1. customat 0° C
2. customwas allowed to room temperature
3. temperatureAfter cooling to room temperature
4. concentrationthe mixture was concentrated in vacuo
5. customquenched by the addition of water at 0° C
6. extractionThe mixture was extracted with EtOAc
7. washThe combined extracts were washed with brine
8. dry with materialdried over Na2SO4
9. customevaporated
10. customThe residue was chromatographed on silica gel [60 g, CHCl3/MeOH (50/1)]

ORD record

ord-ca99caf4592f45e1b240a08abf7c9035

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07179819B2