Water → HCID 131734573, compound

HRID 595190Notes

Reaction equation

HRID 595190 reaction equation
C([Mg]Cl)(C)C.[CH3:6][O:7][C:8]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:9]=1[CH2:10][N:11]1[C:15](=[O:16])[CH2:14][CH:13]([C:17]([O-:19])=O)[CH2:12]1.[CH3:26][O:27][NH:28][CH3:29].O>C1COCC1>[CH3:6][O:7][C:8]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:9]=1[CH2:10][N:11]1[C:15](=[O:16])[CH2:14][CH:13]([C:17]([N:28]([O:27][CH3:26])[CH3:29])=[O:19])[CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 14232N,O-DimethylhydroxylamineHCID 74731155HCID 74731155, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 131734573HCID 131734573, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Isopropylmagnesium chloride (15.3 mL, 30.6 mmol) was added to a solution of 1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylate (3.0 g, 10 mmol) and O,N-dimethyl-hydroxylamine (1.5 g, 15 mmol) in THF (100 mL) at −10° C. The mixture was stirred at 0° C. for 1 hour then the mixture was added to water and concentrated under reduced pressure to afford 1-(2,4-dimethoxybenzyl)-N-methoxy-N-methyl-5-oxopyrrolidine-3-carboxamide. 1H NMR (400 MHz, CDCl3) δ 7.13-7.15 (m, 1H), 6.43-6.45 (m, 2H), 4.41-4.42 (m, 2H), 3.79-3.82 (m, 6H), 3.67 (s, 3H), 3.46-3.49 (m, 3H), 3.18 (s, 3H), 2.70-2.77 (m, 1H), 2.57-2.63 (m, 1H). MS ESI calc'd. for C16H23N2O5 [M+H]+ 323. found 323.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b52840deaa654396a53fef3e6c1f6d05
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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