Water → tert-Butyl (2R,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(cyanomethyl)pyrrolidine-1-carboxylate
반응식
[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([CH2:21]OS(C)(=O)=O)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C-:27]#[N:28].[Na+].O>CS(C)=O>[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[C@H:11]([CH2:21][C:27]#[N:28])[CH2:10]1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]참가 물질
5
반응물 3
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- 80 °C
실험 절차
The mixture of tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-{[(methylsulfonyl)oxy]methyl}pyrrolidine-1-carboxylate (13.95 g, 32.6 mmol, J. Med. Chem. 1988, 31, 1598-611) and sodium cyanide (3.20 g, 65.2 mmol) in dimethylsulfoxide (100 mL) was stirred at 80° C. for 20 h. After cooling to room temperature, water (200 mL) was added to the mixture. The resulting mixture was extracted with ethyl acetate (400 mL×2). The combined organic layer was washed with water (200 mL), brine (200 mL), dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (5:1) to give 7.81 g (70%) of the title compound as a colorless oil.
후처리
- temperatureAfter cooling to room temperature
- extractionThe resulting mixture was extracted with ethyl acetate (400 mL×2)
- washThe combined organic layer was washed with water (200 mL), brine (200 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (5:1)
출처 및 근거
- ORD 기록
- ord-70588ff01ed44ac389f7150c5423bcdf
- 출처 데이터셋
- uspto-grants-2011_03
- 특허 번호
- US07906532B2
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