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

HRID 503913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503913
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-563a31a9d3b14f44a4f4c7a623129a0f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776910B2

Notizen zur Reaktion

Wird geladen…