Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate → HCID 71114188, compound

HRID 710186Notes

Reaction equation

HRID 710186 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[C:16]([C:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1.FC(F)(F)S(OC1CCN(C(OC(C)(C)C)=O)CC=1)(=O)=O>CO.[Pd]>[F:32][C:2]([F:1])([F:31])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[C:16]([CH:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:20][CH2:19]4)[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 71257282HCID 71257282, compound2×

Product 1

HCID 71114188HCID 71114188, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Following the general procedure, tert-butyl 4-[2-(4-(trifluoromethyl)phenyl]benzo[d]oxazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (260 mg) was prepared from intermediate 55 (420 mg, 1.08 mmol) and tert-butyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (358 mg, 1.08 mmol). tert-butyl 4-[2-(4-(trifluoromethyl)phenyl]benzo[d]oxazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (260 mg, 0.58 mmol) was dissolved in methanol (8 ml) and added Pd/C (5%) (520 mg). This mixture was stirred under H2 pressure (6.5 kg) for 12 h. Combined methanol fractions were evaporated on rotavapour to obtain the crude. Crude was purified on combiflash using a gradient mixture of EtOAc and Petether (1:9) as eluent to afford the titled compound (150 mg) as a white solid. M. P.: 174-179° C. MS (m/z): 446.46 [M+H]+.

Workup

  1. customCombined methanol fractions were evaporated on rotavapour
  2. customto obtain the crude
  3. customCrude was purified on combiflash
  4. additiona gradient mixture of EtOAc and Petether (1:9) as eluent

Sources & evidence

ORD record
ord-09738365fc404b918ec066022a014cc6
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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