Hydrochloric Acid → (3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylic acid hydrochloride

HRID 29723Notes

Reaction equation

HRID 29723 reaction equation
[C:1]([N:5]1[CH2:9][C@@H:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])[C@H:7]([C:18]([O:20]C)=[O:19])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C[Si](C)(C)[O-].[K+].[ClH:28]>C(OCC)C.CCOC(C)=O>[ClH:28].[C:1]([N:5]1[CH2:9][C@@H:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])[C@H:7]([C:18]([OH:20])=[O:19])[CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668039Potassium trimethylsilanolateHCID 60122969Methyl (3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate

Product 1

HCID 67212109(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  1. customthe volatiles were evaporated

Sources & evidence

ORD record
ord-59ba43cdbe284ab3be9b924bd16d94bc
Source dataset
uspto-grants-2008_09
Patent number
US07419990B2

Reaction notes

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