Tetrabutylammonium Fluoride → (S)-3-(4-mercapto-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 503926ノート

反応式

HRID 503926 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:18]=[CH:17][C:16]([S:19]CC[Si](C)(C)C)=[CH:15][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.OS([O-])(=O)=O.[K+].[O-]S([O-])(=O)=O.[Na+].[Na+]>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 3

HCID 2724141Tetrabutylammonium FluorideHCID 59428461(S)-3-[4-(2-trimethylsilanyl-ethylsulfanyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 86586342KHSO4 Na2SO4

生成物 1

HCID 59428410(S)-3-(4-mercapto-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester収率 64%

実験手順

A mixture of (S)-3-[4-(2-trimethylsilanyl-ethylsulfanyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (613 mg, 1.615 mmol) and tetrabutylammoniumfluoride (1.0 M in THF, 10.5 mL) was stirred overnight. A solution of 10% KHSO4/Na2SO4 was then added and the resulting mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 91/9) to give 288 mg (64% yield) of (S)-3-(4-mercapto-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a colorless oil.

後処理

  1. extractionthe resulting mixture was extracted with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified via flash chromatography (hexane/EtOAc, 91/9)

出典と根拠

ORDレコード
ord-0af32b28c74c45e1a56c108d593eb33f
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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