Water → (S)-3-(4-bromo-2-hydroxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 503924ノート

反応式

HRID 503924 の反応式
C([S-])C.[Na+].[C:5]([O:9][C:10]([N:12]1[CH2:16][CH2:15][C@@H:14]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=2[O:24]C)[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].OS([O-])(=O)=O.[K+].[O-]S([O-])(=O)=O.[Na+].[Na+].O>CN(C=O)C>[C:5]([O:9][C:10]([N:12]1[CH2:16][CH2:15][C@@H:14]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=2[OH:24])[CH2:13]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

参加物

6

反応物 4

HCID 962WaterHCID 4459711Sodium ethanethiolateHCID 66877312(S)-3-(4-bromo-2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 86586342KHSO4 Na2SO4

生成物 1

HCID 59428430(S)-3-(4-bromo-2-hydroxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester収率 81.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
105 °C

実験手順

Sodium ethanethiolate (80%, 218.7 mg, 1.704 mmol) was added to a solution of (S)-3-(4-bromo-2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (303 mg, 0.8505 mmol) in DMF (3.1 mL) under argon atmosphere. The reaction mixture was heated at 105° C. for 3.5 hours, then cooled to 5° C. A solution of 10% KHSO4/Na2SO4 was added until pH reached 2-3. Water was added, and the resulting mixture was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, with a gradient from 90/10 to 85/15) to give 236 mg (81% yield) of (S)-3-(4-bromo-2-hydroxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a foam.

後処理

  1. temperaturecooled to 5° C
  2. extractionthe resulting mixture was extracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified via flash chromatography (hexane/EtOAc

出典と根拠

ORDレコード
ord-f026644fd6714ffe8ed5dce0271dbc28
出典データセット
uspto-grants-2010_08
特許番号
US07776910B2

反応ノート

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