Ethyl Acetate → 2-Methyl-1-[(R)-1-(2-methyl-4-nitro-phenyl)-pyrrolidin-3-ylamino]-propan-2-ol

HRID 69486

Reaction equation

[Li+].[Br-].[CH3:3][C:4]1([O:7][CH2:6]1)[CH3:5].F[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[N:18]1[CH2:22][CH2:21][C@@H:20]([NH2:23])[CH2:19]1.[C:24](OCC)(=O)C>CN1C(=O)CCC1.O>[CH3:3][C:4]([OH:7])([CH3:5])[CH2:6][NH:23][C@@H:20]1[CH2:21][CH2:22][N:18]([C:10]2[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:9]=2[CH3:24])[CH2:19]1

Participants

Conditions

Temperature: 80 °C

Procedure

LiBr (153.6 mg) and isobutylene oxide (85.1 mg) were added to a solution of (R)-1-(2-fluoro-4-nitro-phenyl)-pyrrolidin-3-ylamine (100 mg) in NMP (2 mL) and the reaction mixture was heated for 2 d at 80° C. Then ethyl acetate and water were added to the mixture. The aqueous phase was extracted several times with ethyl acetate. The organic phases were combined, dried over sodium sulfate and the solvent was removed in vacuum. The raw product was purified by preparative HPLC. In this way the product was obtained with molecular weight 297.15 (C14H20FN3O3); MS (ESI): 298 (M+H+).

Workup

extractionThe aqueous phase was extracted several times with ethyl acetate
dry with materialdried over sodium sulfate
customthe solvent was removed in vacuum
customThe raw product was purified by preparative HPLC
customIn this way the product was obtained with molecular weight 297.15 (C14H20FN3O3)

Sources & evidence

ORD record: ord-c9b57c8025e042e8b0831d2a6c1beb41
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822495B2

Linked notes

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