N,N'-Dimethylethylenediamine → 4-((benzyloxy)methyl)-1-(1-methyl-1H-pyrazol-3-yl)pyrrolidin-2-one

HRID 632754Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH:10]1[CH2:14][NH:13][C:12](=[O:15])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:17]1[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>COC1CCCC1.C(OCC)(=O)C.[Cl-].[NH4+].[Cu]I>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:14][N:13]([C:17]2[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=2)[C:12](=[O:15])[CH2:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-((benzyloxy)methyl)pyrrolidin-2-one (836 mg), 3-iodo-1-methyl-1H-pyrazole (856 mg), copper(I) iodide (80 mg) and tripotassium phosphate (1.7 g) in cyclopentyl methyl ether (20 mL) was added N1,N2-dimethylethane-1,2-diamine (87 μL). The reaction mixture was stirred at 120° C. for 22 hr, and diluted with ethyl acetate, and saturated aqueous ammonium chloride solution was added thereto. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.1 g).

Workup

additionwas added
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-cd70b9c246024d679cf64002631d9de2
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321757B2

Reaction notes

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