Reaktion #58001

ord-59ba43cdbe284ab3be9b924bd16d94bc

Reaktionsgleichung

COC(=O)[C@@H]1CN(C(C)(C)C)C[C@H]1c1ccc(F)cc1F
methyl (3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate
C[Si](C)(C)[O-].[K+]
potassium trimethylsilanolate
Cl
hydrogen chloride
→
CC(C)(C)N1C[C@@H](C(=O)O)[C@H](c2ccc(F)cc2F)C1.Cl
80
CC(C)(C)N1C[C@@H](C(=O)O)[C@H](c2ccc(F)cc2F)C1.Cl
(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylic acid hydrochloride salt

Edukte

—
79
COC(=O)[C@@H]1CN(C(C)(C)C)C[C@H]1c1ccc(F)cc1F
methyl (3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate
C[Si](C)(C)[O-].[K+]
potassium trimethylsilanolate
Cl
hydrogen chloride

Reagenzien

Keine

Lösungsmittel

CCOCC
diethyl ether
CCOC(C)=O
EtOAc

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe volatiles were evaporated

Vorschrift

A mixture of the methyl (3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate enantiomer 79 (1.37 g, 4.61 mmol) and potassium trimethylsilanolate (0.68 g, 5.30 mmol) in diethyl ether (23 mL) was stirred at r.t. overnight. A saturated solution of hydrogen chloride in EtOAc was then added, the volatiles were evaporated to give 80, which was used without further purification in the preparation of Examples detailed below.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07419990B2uspto-grants-2008_09