Ammonium formate → 3-(3,5-Difluorophenyl)-3-methoxypyrrolidine

HRID 575947Notes

Reaction equation

HRID 575947 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=2)([O:13][CH3:14])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[F:22][C:17]1[CH:16]=[C:15]([C:10]2([O:13][CH3:14])[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:20]=[C:19]([F:21])[CH:18]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 199358491-Benzyl-3-(3,5-difluorophenyl)-3-methoxypyrrolidine

Product 1

HCID 199358743-(3,5-Difluorophenyl)-3-methoxypyrrolidineYield 79.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (−)-1-benzyl-3-(3,5-difluorophenyl)-3-methoxypyrrolidine (0.43 g, 1.41 mmol), mlammoniumformate (0.18 g, 2.83 mmol) and palladium on carbon (10%, 0.08 g) in ethanol (10 ml), was refluxed for 40 min. Additional ammoniumformate (0.18 g, 2.83 mmol) was added and after 90 min reflux all starting material was consumed. The reaction mixture was allowed to reach ambient temperature and filtrated over a pad of celite and the solvent was evaporated. The remaining oil was dissolved in methylen chloride and potassium carbonate (2 g), was added. The mixture was stirred over night, filtrated and evaporated to give the title compound (0.24 g, 79%). [a]D=−2.1° (methanol). The amine was converted to the oxalic acid salt and recrystallized from methanol/diethyl ether: M.p. 185-187° C. MS m/z (rel. intensity, 70 eV) 213 (M+, 1), 198 (58), 183 (bp), 171 (84), 141 (55).

Workup

  1. temperaturewas refluxed for 40 min
  2. temperaturereflux all starting material
  3. customwas consumed
  4. customto reach ambient temperature
  5. filtrationfiltrated over a pad of celite
  6. customthe solvent was evaporated
  7. dissolutionThe remaining oil was dissolved in methylen chloride
  8. additionpotassium carbonate (2 g), was added
  9. filtrationfiltrated
  10. customevaporated

Sources & evidence

ORD record
ord-dc4b34416fb64b78a965f36ea6259dbf
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

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