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Tetrabutylammonium Fluoride → 3-(4-Mercapto-2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 503913
Notes
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Reaction equation

HRID 503913 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([N:26]1[CH2:30][CH2:29][CH:28]([C:31]2[CH:36]=[CH:35][C:34]([S:37]CC[Si](C)(C)C)=[CH:33][C:32]=2[O:44][CH3:45])[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].OS([O-])(=O)=O.[K+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[C:19]([O:23][C:24]([N:26]1[CH2:30][CH2:29][CH:28]([C:31]2[CH:36]=[CH:35][C:34]([SH:37])=[CH:33][C:32]=2[O:44][CH3:45])[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 668782423-[2-Methoxy-4-(2-trimethylsilanyl-ethylsulfanyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 86586342KHSO4 Na2SO4

Product 1

HCID 594283563-(4-Mercapto-2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of tetrabutylammoniumfluoride (1.0 M in THF, 9.3 mL) was added to a solution of 3-[2-methoxy-4-(2-trimethylsilanyl-ethylsulfanyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.380 g, 0.9275 mmol) in THF (5 mL) and the reaction mixture was stirred at room temperature for 30 minutes. A solution of 10% KHSO4/Na2SO4 was added and the resulting mixture was extracted 3 times with EtOAc. The combined organic extracts were washed with water and brine; and then dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude material was purified via flash chromatography (hexane/EtOAc/AcOH, 80/20/0.1) to give 0.178 g (62% yield) of 3-(4-mercapto-2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a clear oil.

Workup

  1. extractionthe resulting mixture was extracted 3 times with EtOAc
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialand then dried over Na2SO4
  4. customThe solvent was evaporated under reduced pressure
  5. customthe crude material was purified via flash chromatography (hexane/EtOAc/AcOH, 80/20/0.1)

Sources & evidence

ORD record
ord-563a31a9d3b14f44a4f4c7a623129a0f
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07776910B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes