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

HRID 15077

反応式

HRID 15077 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-85ad0e45c6a6422c9234ea193065d75c
出典データセット
uspto-grants-2010_06
特許番号
US07732456B2

関連ノート

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