3,3-Diphenyl-2-pyrrolidinone → 3,3-Diphenylpyrrolidine

HRID 1667079Notes

Reaction equation

HRID 1667079 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH2:10][NH:9][C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 2382533,3-Diphenyl-2-pyrrolidinoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 4182423,3-Diphenylpyrrolidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 500 mL flask containing 3,3-diphenylpyrrolidine-2-one (5.00 g, 21 mmol; Example 1A) as a suspension in ether (300 mL) was added lithium aluminum hydride (2.0 M in tetrahydrofuran, 24 mL, 48 mmol) slowly via syringe under nitrogen. The reaction was refluxed overnight, cooled to room temperature, and then carefully quenched by the slow addition of 1 N NaOH (60 mL). The reaction was diluted with ethyl acetate (200 mL) and filtered through a pad of diatomaceous earth. The organic phase was separated, concentrated, and the residue purified over silica gel eluting with 95:5 dichloromethane/methanol to give the title compound. MS (DCI+) m/z 224 (M+H)+.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. customcarefully quenched by the slow addition of 1 N NaOH (60 mL)
  3. additionThe reaction was diluted with ethyl acetate (200 mL)
  4. filtrationfiltered through a pad of diatomaceous earth
  5. customThe organic phase was separated
  6. concentrationconcentrated
  7. customthe residue purified over silica gel eluting with 95:5 dichloromethane/methanol

Sources & evidence

ORD record
ord-23a1c3cad23c4b7faf46f13cc86a34a3
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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