Triphenylphosphine → 1-Piperidinecarboxylic acid, 4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-, 1,1-dimethylethyl ester

HRID 1477585Notes

Reaction equation

HRID 1477585 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:7]=[CH:6][NH:5][N:4]=1.O[CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[F:1][C:2]([F:9])([F:8])[C:3]1[CH:7]=[CH:6][N:5]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[N:4]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 18070343-(Trifluoromethyl)pyrazole

Product 1

HCID 712265361-Piperidinecarboxylic acid, 4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-, 1,1-dimethylethyl esterYield 45.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution (1.0 mL) of 3-(trifluoromethyl)-1H-pyrazole (272 mg, 2.00 mmol), tert-butyl 4-hydroxy-piperidine-1-carboxylate (402 mg, 2.00 mmol), and triphenylphosphine (629 mg, 2.40 mmol), diisopropyl azodicarboxylate (1.36 mL, 2.60 mmol, toluene solution) was added at room temperature and the resultant solution was stirred at room temperature for 22 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure and purified by preparative liquid chromatography to obtain the title compound (289 mg, yield 45%).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. custompurified by preparative liquid chromatography

Sources & evidence

ORD record
ord-ef4c689b738545689392f48c02c3eaec
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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