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Water → (R)-4-Acetyl-1-[4-(3-fluoro-benzyloxy)-phenyl]-pyrrolidin-2-one

HRID 273184
Notes
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Reaction equation

HRID 273184 reaction equation
CON(C)[C:4]([C@@H:6]1[CH2:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)=[CH:14][CH:13]=2)[CH2:7]1)=[O:5].[CH3:28][Mg]Br.O.C(OCC)(=O)C>O1CCCC1.C1CCCCC1>[C:4]([C@H:6]1[CH2:7][N:8]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)=[CH:16][CH:17]=2)[C:9](=[O:11])[CH2:10]1)(=[O:5])[CH3:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 86602842(R)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methoxy-methyl-amideHCID 178418573HCID 178418573, compound

Product 1

HCID 11609560(R)-4-Acetyl-1-[4-(3-fluoro-benzyloxy)-phenyl]-pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8078CyclohexaneSolvent

Conditions

Temperature
0 °C

Procedure

(R)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methoxy-methyl-amide (0.050 g, 0.143 mmol) was dissolved under argon in tetrahydrofurane (1 ml) and methyl magnesium bromide (0.188 mmol, 0.063 ml) was added at 0° C. The resulting solution was stirred at 0° C. for two hours. Water was added at 0° C. and the mixture was stirred for one hour. Extraction with ethyl acetate gave a residue which after chromatography on silica gel using a 9:1-mixture of ethyl acetate and cyclohexane as the eluent yielded 0.040 g (91% of theory) of the title compound as a white solid. MS: m/e=328.4 (M+H)+.

Workup

  1. stirringthe mixture was stirred for one hour
  2. extractionExtraction with ethyl acetate
  3. customgave a residue which after chromatography on silica gel using a 9

Sources & evidence

ORD record
ord-52e7da186f734bc6844fcbe0b570d6bf
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07456210B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes