Pyrrolidine → HCID 68766810, compound

HRID 1171756Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:16][C:17](=[O:26])[CH2:18][N:19]1[CH:23]=[C:22]([CH:24]=O)[CH:21]=[N:20]1)[CH3:15].N1CCCC1>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12]/[C:11](=[CH:24]\[C:22]2[CH:21]=[N:20][N:19]([CH2:18][C:17]([O:16][CH2:14][CH3:15])=[O:26])[CH:23]=2)/[C:10](=[O:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-(t-butoxycarbonyl)pyrrolidin-3-one (6.8 g) in ethanol (200 ml) were added ethyl(4-formyl-1H-pyrazol-1-yl)acetate (8.0 g) and pyrrolidine (600 μl). The resulting mixture was stirred at 80° C. for 45 minutes, cooled to room temperature, and the solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel using a mixture of hexane, ethyl acetate and dichloromethane (2:1:1) as the eluent to afford the title compound as a yellow amorphous solid (4.47 g, yield: 35%).

Workup

temperaturecooled to room temperature
customthe solvent was evaporated in vacuo
customThe residue was purified by chromatography on silica gel using
additiona mixture of hexane, ethyl acetate and dichloromethane (2:1:1) as the eluent

Sources & evidence

ORD record: ord-e0beed6f4e304f088a5126da10ca4542
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829580B2

Reaction notes

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