Ammonium formate → 3-(3,4-Difluorophenyl)pyrrolidin-3-ol

HRID 1931859Notes

Reaction equation

HRID 1931859 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)([OH:13])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[F:21][C:16]1[CH:15]=[C:14]([C:10]2([OH:13])[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:19]=[CH:18][C:17]=1[F:20]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 671736601-Benzyl-3-(3,4-difluorophenyl)pyrrolidin-3-ol

Product 1

HCID 635869723-(3,4-Difluorophenyl)pyrrolidin-3-olYield 105.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 1-benzyl-3-(3,4-difluorophenyl)pyrrolidin-3-ol (0.55 g, 1.9 mmol) and ammonium formiate (0.36 g, 5.7 mmol) in ethanol (20 mL) was added palladium on carbon (0.11 g) and the mixture was refluxed for 1 h, cooled to ambient temperature and filtered through a pad of celite. The filtrate was evaporated to give the title compound (0.4 g). MS m/z (rel. intensity, 70 eV) 199 (M+, bp), 180 (51), 150 (60), 141 (90), 113 (75).

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. filtrationfiltered through a pad of celite
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-12c19e1106b54ea88499072f5d6b6d5a
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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