N-Methylethylamine → HCID 67092538, compound

HRID 2068258Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1([CH2:20]I)[CH:9]([CH3:10])[C:8](=[O:11])[N:7]([C:12]2[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:19])[CH2:6]1)=[O:4].[CH2:22]([NH:24][CH3:25])[CH3:23]>CC#N>[CH3:1][O:2][C:3]([C:5]1([CH2:20][N:24]([CH2:22][CH3:23])[CH3:25])[CH:9]([CH3:10])[C:8](=[O:11])[N:7]([C:12]2[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:19])[CH2:6]1)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-(2,6-dimethylphenyl)-3-iodomethyl-4-methyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (prepared from step d, 100 mg, 0.25 mmol) in CH3CN (3 mL) was added N-ethylmethylamine (215 μL, 2.5 mmol) and stirred at 80° C. for overnight. Volatiles were evaporated under reduced pressure and purified by automated flash chromatography (SiO2, 20→70% EtOAc/hexanes) to obtain 1-(2,6-dimethyl-phenyl)-3-[(ethylmethylamino)-methyl]-4-methyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (10 mg, 12% yield). LC-MS: Rt (retention time): 0.61 min, MS: (ES) m/z 333.3 (M+H+).

Workup

customVolatiles were evaporated under reduced pressure
custompurified by automated flash chromatography (SiO2, 20→70% EtOAc/hexanes)

Sources & evidence

ORD record: ord-0c6f767050aa4239a35d1a8ac69f2720
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293925B2

Reaction notes

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