tert-Butyl 3-cyano-4-oxopyrrolidine-1-carboxylate → HCID 86639709, compound

HRID 2264306Notes

Reaction equation

HRID 2264306 reaction equation
[C:1]([CH:3]1[C:7](=O)[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)#[N:2].[CH3:16][C:17]1[CH:21]=[C:20]([NH2:22])[NH:19][N:18]=1>C(O)C>[NH2:2][C:1]1[N:19]2[N:18]=[C:17]([CH3:16])[CH:21]=[C:20]2[N:22]=[C:7]2[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][C:3]=12

Participants

4

Reactant 2

HCID 2756790tert-Butyl 3-cyano-4-oxopyrrolidine-1-carboxylateHCID 178418690HCID 178418690, compound

Product 1

HCID 86639709HCID 86639709, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 250 mg (1.19 mmol) of tert-butyl 3-cyano-4-oxopyrrolidine-1 carboxylate in ethanol (5 mL) was added 115 mg (1.19 mmol) of 3-methyl-1H-pyrazol-5-amine. The reaction mixture was refluxed for 1 h, cooled to ambient temperature and the solvent evaporated in vacuo. The resulting residue was chromatographed on a Biotage Horizon® system (silica gel, 0 to 100% ethyl acetate/hexanes gradient) to yield the title compound as a white solid. LC/MS 290.1 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. customthe solvent evaporated in vacuo
  3. customThe resulting residue was chromatographed on a Biotage Horizon® system (silica gel, 0 to 100% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-a7b01322555c482297c6d1c41926b1b0
Source dataset
uspto-grants-2010_12
Patent number
US07855206B2

Reaction notes

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