Formic Acid → 1-Benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine

HRID 62635Notes

Reaction equation

HRID 62635 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][C:10]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=2)([C:13]([F:16])([F:15])[F:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)=O.[H][H]>CO.[Pt].C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([C:17]2[CH:18]=[C:19]([Cl:24])[CH:20]=[C:21]([Cl:23])[CH:22]=2)([C:13]([F:16])([F:15])[F:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 284Formic Acid2×HCID 118270793HCID 118270793, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 582188831-Benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidineYield 96%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalyst3×HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,3-dihydro-1H-pyrrole (200 mg, 82% purity, 440 μmol) was dissolved in methanol (5 mL) under an argon atmosphere. Formic acid (200 μL, 5.30 mmol) and platinum on charcoal (5 w/w % Pt/C, ˜60% H2O, 42.9 mg, 4.4 μmol) was added and the flask was charged with hydrogen (balloon). The reaction was stirred for six hours at room temperature and then left standing over night. After the addition of platinum on charcoal (0.5 mol %) and formic acid (1 mL) the reaction mixture was warmed to 40-50° C. for six hours and then left standing at room temperature. Refluxing the mixture for three more hours and addition of more platinum on charcoal (1.0 mol %) after one hour led to complete conversion. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (5 mL), filtered over celite, washed with saturated sodium bicarbonate and brine solution. The organic phase was dried over sodium sulfate, filtered and the solvents evaporated. 1-benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine was obtained (163 mg, 97% purity, 96% yield).

Workup

  1. waitleft
  2. waitstanding over night
  3. temperaturewas warmed to 40-50° C. for six hours
  4. waitleft
  5. customstanding at room temperature
  6. temperatureRefluxing the mixture
  7. temperatureThe reaction mixture was cooled to room temperature
  8. filtrationfiltered over celite
  9. washwashed with saturated sodium bicarbonate and brine solution
  10. dry with materialThe organic phase was dried over sodium sulfate
  11. filtrationfiltered
  12. customthe solvents evaporated

Sources & evidence

ORD record
ord-432e98c9b7334ac2b9a7ed6b74537ade
Source dataset
uspto-grants-2016_09
Patent number
US09447036B2

Reaction notes

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