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

HRID 1890682Notes

Reaction equation

HRID 1890682 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>C(O)C>[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)pyrrolidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In step 6A-3, sodium borohydride (2.1 g, 55.2 mmol) was added at room temperature to a solution of 5-(2,5-difluorophenyl)-3,4-dihydro-2H-pyrrole (6-4) (5.0 g, 28 mmol) in anhydrous ethanol (150 mL). The reaction mixture was stirred over-night at room temperature. The ethanol was removed using a rotary evaporator and the resulting orange solid was reconstituted with ethyl acetate. The organic layer was washed with brine (3×150 mL), dried with sodium sulfate and the. ethyl acetate was removed to yield 2-(2,5-difluorophenyl)pyrrolidine (6-5) as a light yellow oil. m/z=184.2 [M+1].

Workup

  1. customThe ethanol was removed
  2. customa rotary evaporator
  3. washThe organic layer was washed with brine (3×150 mL)
  4. dry with materialdried with sodium sulfate
  5. customethyl acetate was removed

Sources & evidence

ORD record
ord-d911cd8a478e43d4ae312e818155d80c
Source dataset
uspto-grants-2013_08
Patent number
US08507488B2

Reaction notes

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