Hydrochloric Acid → (2S,4R)-Tert-butyl 2-(hydroxymethyl)-4-(methylsulfonyloxy)pyrrolidine-1-carboxylate
반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][C@H:9]1[C:18](OC(OCC)=O)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:14]([CH3:17])(=[O:15])=[O:16])[CH2:10][C@H:9]1[CH2:18][OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]참가 물질
반응 조건
- 온도
- -40 °C
실험 절차
To the resulting reaction mixture containing (2S,4R)-1-t-butoxycarbonyl-2-ethoxycarbonyloxycarbonyl-4-methane sulfonyloxypyrrolidine obtained in Step D-3 cooling at -40° C., tetra-n-butylammonium bromide (11.8 g: 0.0365 mole) and a solution of sodium borohydride (52.5 g: 1.35 mole) in water (55 ml) are added. The mixture is allowed to warm to -10° C. and stirred for 1 hour. The aqueous layer is acidified with dilute hydrochloric acid to pH 3. The organic layer is taken, successively washed with aqueous sodium hydrogen carbonate and water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue is recrystallized from a toluene-hexane mixture to give (2S,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol (101.3 g). Yield: 94%. Colorless crystals. mp. 95° to 96° C.
후처리
- customTo the resulting reaction mixture
- temperatureto warm to -10° C.
- washsuccessively washed with aqueous sodium hydrogen carbonate and water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue is recrystallized from a toluene-hexane mixture
출처 및 근거
- ORD 기록
- ord-446c1538a699481cb678e27f38eea041
- 출처 데이터셋
- uspto-grants-1997_12
- 특허 번호
- US05703243
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