Ethanol → 3-(2,3-Difluorophenyl)pyrrolidin-3-ol

HRID 1931895Notes

Reaction equation

HRID 1931895 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=2[F:21])([OH:13])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+].C(O)C>[Pd].ClCCl.C(OC)(C)(C)C>[F:21][C:15]1[C:16]([F:20])=[CH:17][CH:18]=[CH:19][C:14]=1[C:10]1([OH:13])[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

6

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 685158491-Benzyl-3-(2,3-difluorophenyl)pyrrolidin-3-ol

Product 1

HCID 639883833-(2,3-Difluorophenyl)pyrrolidin-3-olYield 50.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21918119Dcm mtbeSolvent

Procedure

Preparation according to preparation 4: (+)-1-benzyl-3-(2,3-difluorophenyl)pyrrolidin-3-ol (2.86 g, 9.88 mmol), ammonium formiate (1.25 g, 19.76 mmol), ethanol (50 mL) and palladium on carbon (130 mg). Refluxed for 90 min. Dichloromethane/methyl tert-butyl ether (1:1, 50 mL) was added and the mixture was filtrated through celite, the filtrate was evaporated and purified by flash column chromatography on silica gel (triethylamine/methanol, 0:1 to 1:4) to give the title compound (1.0 g). MS m/z (relative intensity, 70 eV) 199 (M+, bp), 141 (84), 113 (65), 127 (64), 63 (48).

Workup

  1. customPreparation
  2. customaccording to preparation 4
  3. temperatureRefluxed for 90 min
  4. filtrationthe mixture was filtrated through celite
  5. customthe filtrate was evaporated
  6. custompurified by flash column chromatography on silica gel (triethylamine/methanol, 0:1 to 1:4)

Sources & evidence

ORD record
ord-7169aae4fac14af3b28fa46a137bafed
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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