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

HRID 503926노트

반응식

HRID 503926 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0af32b28c74c45e1a56c108d593eb33f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776910B2

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