Sodium borohydride → 2-(2,5-Difluorophenyl)pyrrolidine

HRID 926697Notes

Reaction equation

HRID 926697 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[C:11]1[CH2:12][CH2:13][CH2:14][N:15]=1>CO.O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[CH:11]1[CH2:12][CH2:13][CH2:14][NH:15]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 583357265-(2,5-difluorophenyl)-3,4-dihydro-2H-pyrrole

Product 1

HCID 246978582-(2,5-Difluorophenyl)pyrrolidineYield 79.8%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

NaBH4(12 g, 314.9 mmol) was added to a solution of 5-(2,5-difluorophenyl)-3,4-dihydro-2H-pyrrole (28.5 g, 157.4 mmol) in a mixture of MeOH:H2O (4:1, 250 mL) and stirring was continued at 25-35° C. for 2 h. The reaction mixture was quenched with 1N aqueous HCl solution and basified with 2N aqueous NaOH solution, extracted with DCM, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 23 g of the title compound.

Workup

  1. customThe reaction mixture was quenched with 1N aqueous HCl solution
  2. extractionextracted with DCM
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f4a355857a18467f97427fe520ea0966
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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