Triphenylphosphine → t-Butyl 4-(4-trifluoromethylsulfanyl-phenoxy)piperidine-1-carboxylate

HRID 1792506Notes

Reaction equation

HRID 1792506 reaction equation
[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([F:4])[F:3].O[CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O>[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[CH:8][CH:7]=1)([F:4])[F:3]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 38151584-(Trifluoromethylsulfanyl)phenol

Product 1

HCID 22031376t-Butyl 4-(4-trifluoromethylsulfanyl-phenoxy)piperidine-1-carboxylateYield 79.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2 g 4-trifluoromethylsulfanyl-phenol, 2.07 g t-butyl 4-hydroxy-1-piperidinecarboxylate, 3.2 g triphenyl phosphine and 5.4 g diethyl azodicarboxylate (40% toluene solution) in anhydrous tetrahydrofuran (40 mL) was heated for 24 hours under reflux in a stream of nitrogen. Water was added thereto, and the reaction solution was extracted with ethyl acetate, dried over sodium sulfate, and purified by NH silica gel chromatography (hexane/ethyl acetate) to give 3.07 g of the title compound.

Workup

  1. temperatureunder reflux in a stream of nitrogen
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. custompurified by NH silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-974ff422334b47ba88b6df9ed7b633cf
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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