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Water → (RS)-1-(4-Benzyloxy-phenyl)-2-oxo-pyrrolidine-3-carbonitrile

HRID 1768128
Notes
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Reaction equation

HRID 1768128 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][CH:17](Br)[C:16]2=[O:21])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:22]#[N:23].[Na+].[I-].[Na+].O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][CH:17]([C:22]#[N:23])[C:16]2=[O:21])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 8929Sodium CyanideHCID 23614761(RS)-1-(4-benzyloxy-phenyl)-3-bromo-pyrrolidin-2-one

Product 1

HCID 9839008(RS)-1-(4-Benzyloxy-phenyl)-2-oxo-pyrrolidine-3-carbonitrileYield 13%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
120 °C

Procedure

300 mg (0.87 mmol) of (RS)-1-(4-benzyloxy-phenyl)-3-bromo-pyrrolidin-2-one is dissolved in 5 ml N,N-dimethylformamide. 64 mg (1.3 mmol) sodium cyanide and 13 mg (0.09 mmol) sodium iodide are added and the suspension stirred for 10 min. at 120° C. The reaction mixture is treated with water and extracted with ethyl acetate to yield 33 mg (13%) of a colorless solid. MS: m/e=293.3 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-022d0db5395449bb9bc685655654da17
Source dataset
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07235581B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes