Aluminium lithium hydride → 3,3-Bis(4-fluorophenyl)pyrrolidine

HRID 1667239Notes

Reaction equation

HRID 1667239 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH2:12][CH2:11][NH:10][C:9]2=O)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 673585653,3-Bis(4-fluorophenyl)pyrrolidin-2-one

Product 1

HCID 673601783,3-Bis(4-fluorophenyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 500 mL flask containing 3,3-bis(4-fluorophenyl)pyrrolidin-2-one (Example 58B, 4.1 g, 15 mmol) as a suspension in ether (300 mL) was added lithium aluminum hydride (2.0 Min tetrahydrofuran, 15 mL, 30 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 97:3 dichloromethane/methanol to give the title compound. MS (DCI+) m/z 260 (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 97:3 dichloromethane/methanol

Sources & evidence

ORD record
ord-dc536e9d329b443cb9082355524e3ceb
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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