Tributylphosphine → tert-Butyl 4-(4-(trifluoromethyl)phenoxy)piperidine-1-carboxylate

HRID 856034Notes

Reaction equation

HRID 856034 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.O[C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1C=CC=CC=1.O>[F:23][C:22]([F:25])([F:24])[C:19]1[CH:20]=[CH:21][C:16]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 678744-(Trifluoromethyl)phenolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 22052586tert-Butyl 4-(4-(trifluoromethyl)phenoxy)piperidine-1-carboxylateYield 44%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

Tert-butyl 4-hydroxypiperidine-1-carboxylate (2.22 g, 10.0 mmol), 4-hydroxybenzotrifluoride (1.21 g, 7.45 mmol), tri-n-butylphosphine (2.26 g, 11.2 mmol) and 1,1′-(azodicarbonyl)dipiperidine (2.82 g, 11.2 mmol) were dissolved in benzene (20 ml), and the mixture was stirred at room temperature for 2 days. To which water was added, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and thereafter filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1) ro afford tert-butyl 4-(4-trifluoromethylphenoxy)piperidine-1-carboxylate (1.13 g, yield 44%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1) ro

Sources & evidence

ORD record
ord-b82a3f7facff4c2480acc6b04b270c7b
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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