Hydrogen chloride-ethyl acetate → HCID 86628541, compound

HRID 732671Notes

Reaction equation

HRID 732671 reaction equation
[C:1]1([C@H:11]([NH:13][CH2:14][C@@H:15]2[C@@H:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][N:17]([C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])[CH2:16]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[ClH:32].C(OCC)(=O)C>C(OCC)(=O)C.CCCCCC>[ClH:32].[C:1]1([C@H:11]([NH:13][CH2:14][C@@H:15]2[C@@H:19]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:18][N:17]([C:26](=[O:31])[C:27]([F:28])([F:29])[F:30])[CH2:16]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86628542HCID 86628542, compound

Product 1

HCID 86628541HCID 86628541, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 389 mg portion of the thus obtained (1R)-1-(1-naphthyl)-N-{[(3S,4S)-4-phenyl-1-(trifluoroacetyl)pyrrolidin-3-yl]methyl}ethanamine was dissolved in 5 ml of ethyl acetate and treated with a 4 M hydrogen chloride/ethyl acetate solution. The reaction solution was diluted with hexane, and the thus precipitated solid was recrystallized from ethyl acetate and hexane to obtain 268 mg of (1R)-1-(1-naphthyl)-N-{[(3S,4S)-4-phenyl-1-(trifluoroacetyl)pyrrolidin-3-yl]methyl}ethanamine hydrochloride as colorless crystals.

Workup

  1. customthe thus precipitated solid was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-828d61b214dc4577b17ba6f465e92f1c
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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