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

HRID 62636Notes

Reaction equation

HRID 62636 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.[BH4-].[Na+].Cl>O1CCCC1>[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 118270793HCID 118270793, compound

Product 1

HCID 582188831-Benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidineYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,3-dihydro-1H-pyrrole (100 mg, 90% purity, 242 μmol) was dissolved in tetrahydrofurane (2 mL) and sodium borohydride (26.0 mg, 677 μmol) was added at room temperature. After 30 minutes at room temperature the reaction mixture was acidified with hydrochloric acid (3.6%) and extracted twice with dichloromethane. The combined organic phases were washed with water, dried over sodium sulfate, filtered and the solvents evaporated. This procedure yielded 1-benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (80.0 mg, 79% purity, 70% yield).

Workup

  1. extractionextracted twice with dichloromethane
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvents evaporated

Sources & evidence

ORD record
ord-35e6ccda475f4404b8484cb5bd581a8d
Source dataset
uspto-grants-2016_09
Patent number
US09447036B2

Reaction notes

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