Triphenylphosphine → tert-Butyl 4-[4-(trifluoromethoxy)phenoxy]piperidine-1-carboxylate

HRID 856101Notes

Reaction equation

HRID 856101 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.[F:15][C:16]([F:26])([F:25])[O:17][C:18]1[CH:23]=[CH:22][C:21](O)=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[F:15][C:16]([F:25])([F:26])[O:17][C:18]1[CH:23]=[CH:22][C:21]([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:20][CH:19]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 70015p-(Trifluoromethoxy)phenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 23081100tert-Butyl 4-[4-(trifluoromethoxy)phenoxy]piperidine-1-carboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl 4-hydroxypiperidine-1-carboxylate (56.5 g, 0.28 mol), 4-trifluoromethoxyphenol (50 g, 0.28 mol) and triphenylphosphine (108 g, 0.42 mol) were dissolved in THF (500 ml). Diethyl azodicarboxylate (65 ml, 0.42 mol) was added dropwise to this solution under reflux, and the mixture was refluxed for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1) to afford tert-butyl 4-(4-trifluoromethoxyphenoxy)-piperidine-1-carboxylate (92 g, yield 91%) as a colorless oil.

Workup

  1. temperatureunder reflux
  2. temperaturethe mixture was refluxed for 5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-00829fe68f4048d8883420c3d5bcafe7
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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