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

HRID 503926Notes

Reaction equation

HRID 503926 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-0af32b28c74c45e1a56c108d593eb33f
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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