N-benzyl-3-pyrrolidinol → 3-[3-(Trifluoromethyl)phenoxy]pyrrolidine

HRID 1093835Notes

Reaction equation

HRID 1093835 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[CH2:9]1)C1C=CC=CC=1.C(N1CCC(O)C1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[F:23][C:20]([F:21])([F:22])[C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[O:13][CH:10]1[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

5

Reactant 2

HCID 69889N-benzyl-3-pyrrolidinolHCID 20263001HCID 20263001, compound

Product 1

HCID 183371713-[3-(Trifluoromethyl)phenoxy]pyrrolidineYield 85.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Pd(OH)2 (125 mg) was added to a stirred solution of 1-benzyl-3-(3-trifluoromethyl-phenoxy)-pyrrolidine (prepared according to Step 1 and 5 of the General Scheme from 1-benzylpyrrolidin-3-ol) (125 mg, 0.4 mmol) in MeOH (15 mL) in an inert atmosphere and stirring was continued under H2 gas atmosphere overnight. The reaction mixture was filtered through celite. The filtrate collected was concentrated under reduced pressure to afford 811 mg (85.9% Yield) of 3-(3-Trifluoromethyl-phenoxy)-pyrrolidine.

Workup

  1. customprepared
  2. filtrationThe reaction mixture was filtered through celite
  3. customThe filtrate collected
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-1b3220de875c43a4ad3fd9681025ae13
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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