Phenacyl bromide → HCID 57344849, compound

HRID 1619540Notes

Reaction equation

HRID 1619540 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:10]([O:12][C@@H:13]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:25][CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:28]>CN(C=O)C.C(#N)C>[Br-:25].[C:1]([O:5][C:6]([NH:8][CH:9]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:10]([O:12][C@@H:13]1[CH2:17][CH2:16][N+:15]([CH3:18])([CH2:26][C:27](=[O:28])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:14]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 6259Phenacyl bromideHCID 67607395HCID 67607395, compound

Product 1

HCID 57344849HCID 57344849, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (R)-1-methylpyrrolidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate (C61) (170 mg, 0.51 mmol) in DMF (5 ml) and acetonitrile (3 ml), was added 2-bromo-1-phenylethanone (111 mg, 0.56 mmol). The reaction was stirred at RT for 15 hours, and the solvent was evaporated. The crude was purified by flash chromatography (DCM/MeOH=9/1) to obtain (3R)-3-(2-(tert-butoxycarbonylamino)-2-phenylacetoxy)-1-methyl-1-(2-oxo-2-phenylethyl)pyrrolidinium bromide (152 mg; 56% yield).

Workup

  1. customthe solvent was evaporated
  2. customThe crude was purified by flash chromatography (DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-d237bc378aba43809001e268f17c5314
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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