Methyl 3-cyano-2-(4-fluorophenyl)propanoate → 3-(4-Fluorophenyl)pyrrolidin-2-one

HRID 1667228Notes

Reaction equation

HRID 1667228 reaction equation
[C:1]([CH2:3][CH:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[C:5](OC)=[O:6])#[N:2]>[Ni].N.CO>[F:15][C:12]1[CH:13]=[CH:14][C:9]([CH:4]2[CH2:3][CH2:1][NH:2][C:5]2=[O:6])=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 67358817Methyl 3-cyano-2-(4-fluorophenyl)propanoate

Product 1

HCID 673577243-(4-Fluorophenyl)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

Methyl 3-cyano-2-(4-fluorophenyl)propanoate (2.09 g, 10.09 mmol; Example 189A) and 7 M NH3-methanol (100 mL) were added to Raney® nickel, solvent washed (20.90 g, 356 mmol) in a 250 mL stainless steel pressure bottle and stirred for 17 hours under hydrogen at 30 psi and room temperature. The mixture was filtered through a nylon membrane and concentrated to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.36-7.16 (m, 2H), 7.12-6.94 (m, 2H), 6.04 (s, 1H), 3.61 (t, J=9.2, 1H), 3.54-3.39 (m, 2H), 2.71-2.53 (m, 1H), 2.23 (ddd, J=8.4, 12.9, 17.7, 1H); MS (ESI+) m/z 179.9 (M+H)+.

Workup

  1. washwashed (20.90 g, 356 mmol) in a 250 mL stainless steel pressure bottle
  2. filtrationThe mixture was filtered through a nylon membrane
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-74163f57a6dd4d2c9e948180ee700174
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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