Tetramethylammonium fluoride → 2-benzyl-2-(1H-indole-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 661537

Reaktionsgleichung

Reaktionsgleichung von HRID 661537
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:13]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([Si](C(C)C)(C(C)C)C(C)C)[CH:19]=[CH:18]2)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N+](C)(C)C.[F-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:13]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[CH:18]2)=[O:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 67803Tetramethylammonium fluorideHCID 666880832-benzyl-2-(1-triisopropylsilanyl-1H-indole-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 666877772-benzyl-2-(1H-indole-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-benzyl-2-(1-triisopropylsilanyl-1H-indole-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.145 g, 0.259 mmol) in THF (5 mL) at ambient temperature under nitrogen was added TMAF (0.026 g, 0.285 mmol). After one hour, the reaction mixture was concentrated in vacuo. Purification of the residue by chromatography (silica, 25-50% EtOAc in hexanes) gave 2-benzyl-2-(1H-indole-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.045 g, 0.111 mmol, 43%) as a colourless foam.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customPurification of the residue by chromatography (silica, 25-50% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2adb49a5e7b54862a385aff8b84be25a
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084623B2

Verknüpfte Notizen

Wird geladen…