Pyridine → (S)-benzyl 2-(2-bromophenylcarbamoyl)-2-methylpyrrolidine-1-carboxylate

HRID 419770Notes

Reaction equation

HRID 419770 reaction equation
Cl[C:2]([C@:4]1([CH3:19])[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])=[O:3].[Br:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[NH2:23].N1C=CC=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1.CN(C)C=O.[Cl-].[Na+].O>[Br:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[NH:23][C:2]([C@:4]1([CH3:19])[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])=[O:3]

Participants

8

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 119922-BromoanilineHCID 86643491(S)-benzyl 2-(chlorocarbonyl)-2-methylpyrrolidine-1-carboxylate

Product 1

HCID 86643492(S)-benzyl 2-(2-bromophenylcarbamoyl)-2-methylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of EXAMPLE 5A in toluene (20 mL) and N,N-dimethylformamide (10 mL) was added 2-bromoaniline (0.891 g) and pyridine (1.38 mL) and the mixture heated at 40° C. for 4 hours. The mixture was treated with ethyl acetate and brine and the organic layer was washed with 5% aqueous citric acid and aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated to afford the title compound.

Workup

  1. washthe organic layer was washed with 5% aqueous citric acid and aqueous sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4eaec1b767ef4e608c986dd8e82c3314
Source dataset
uspto-grants-2012_01
Patent number
US08093396B2

Reaction notes

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