HCID 131734573, compound → HCID 118208857, compound

HRID 595191Notes

Reaction equation

HRID 595191 reaction equation
[CH3:1][Mg+].[Br-].[CH3:4][O:5][C:6]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:7]=1[CH2:8][N:9]1[C:13](=[O:14])[CH2:12][CH:11]([C:15](N(OC)C)=[O:16])[CH2:10]1>C1COCC1.O>[C:15]([CH:11]1[CH2:10][N:9]([CH2:8][C:7]2[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:6]=2[O:5][CH3:4])[C:13](=[O:14])[CH2:12]1)(=[O:16])[CH3:1]

Participants

5

Reactant 2

HCID 131734573HCID 131734573, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 118208857HCID 118208857, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

MeMgBr (2.3 mL, 6.8 mmol) was added to a mixture of 1-(2,4-dimethoxybenzyl)-N-methoxy-N-methyl-5-oxopyrrolidine-3-carboxamide (2.0 g, 6.2 mmol) in THF (40 mL) at −10° C. The mixture was stirred at 0° C. for 1 hour then diluted with water and the mixture was extracted with EtOAc. The EtOAc layer was dried over sodium sulfate and concentrated under reduced pressure to afford 4-acetyl-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one. 1H NMR (400 MHz, CDCl3) δ 7.10-7.13 (m, 1H), 6.43-6.45 (m, 2H), 4.41-4.42 (m, 2H), 3.79-3.82 (m, 6H), 3.46-3.20 (m, 3H), 2.61-2.64 (m, 2H), 2.04-2.15 (d, J=7.2 Hz, 3H). MS ESI calc'd. for C15H20NO4 [M+H]+ 278. found 278.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe EtOAc layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e6bf60423c7e452a9537ab7c3680041b
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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