Ethyl 3-cyano-2,2-bis(4-fluorophenyl)propanoate → 3,3-Bis(4-fluorophenyl)pyrrolidin-2-one

HRID 1667121Notes

Reaction equation

HRID 1667121 reaction equation
[C:1]([CH2:3][C:4]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[C:5](OCC)=[O:6])#[N:2]>C(O)(=O)C.O=[Pt]=O>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:4]2([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:3][CH2:1][NH:2][C:5]2=[O:6])=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 67357361Ethyl 3-cyano-2,2-bis(4-fluorophenyl)propanoate

Product 1

HCID 673585653,3-Bis(4-fluorophenyl)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of the product from Example 58A (20 mg, 0.063 mmol) in acetic acid (4 mL) was added to PtO2 (4.00 mg, 0.018 mmol) in a 50 mL pressure bottle and stirred at room temperature for 12 hours under hydrogen (30 pounds per square inch). The mixture was filtered through a nylon membrane then concentrated to obtain solid. The solid was slurried in 5% ethyl acetate/hexanes, filtered and dried to give the title compound. MS (DCI+) m/z 274 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationthen concentrated
  3. customto obtain solid
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-a019b9adc28e4909a3c4befc3c744cde
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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