Dimethylformamide → tert-butyl (3R)-3-(2-fluoroethoxy)pyrrolidine-1-carboxylate

HRID 15077

반응식

HRID 15077 반응식
[H-].[Na+].CN(C=O)C.[OH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1.C1(C)C=CC(S(O[CH2:31][CH2:32][F:33])(=O)=O)=CC=1>C(OCC)(=O)C>[F:33][CH2:32][CH2:31][O:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 2560192-Fluoroethyl p-ToluenesulfonateHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

생성물 1

HCID 86614896tert-butyl (3R)-3-(2-fluoroethoxy)pyrrolidine-1-carboxylate수율 41%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Sodium hydride (55% oiliness, 140 mg, 3.2 mmols) was added to DMF (5 mL) solution of tert-butyl (3R)-3-hydroxypyrrolidine-1-carboxylate (501.2 mg, 2.7 mmols) and stirred at room temperature for 30 minutes, followed by addition of 2-fluoroethyl p-toluenesulfonate (1.17 g, 5.4 mmols) and further 24 hours' stirring at the same temperature. Ethyl acetate was added to the reaction liquid which then was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (KP-Sil Sil FLASH 25+M, ethyl acetate:hexane=1:10→2:8) to provide the title compound (253 mg, 41%).

후처리

  1. stirringstirring at the same temperature
  2. washthen was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentrating the solvent under reduced pressure
  5. customthe residue was purified on silica gel column chromatography (KP-Sil Sil FLASH 25+M, ethyl acetate:hexane=1:10→2:8)

출처 및 근거

ORD 기록
ord-85ad0e45c6a6422c9234ea193065d75c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732456B2

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