Sodium Carbonate → tert-Butyl 4-[2-(trifluoromethyl)phenyl]-1,2,5,6-tetrahydropyridinecarboxylate

HRID 489668Notes

Reaction equation

HRID 489668 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.FC(F)(F)S(O[C:20]1[CH2:25][CH2:24][NH:23][CH:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:21]=1)(=O)=O.C(OC(N1CCC(=O)CC1)=O)(C)(C)C.[Li+].CC([N-]C(C)C)C.C1C=CC(N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>O.COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:20]1[CH2:25][CH2:24][NH:23][CH:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:21]=1

Participants

10

Reactant 6

HCID 10340Sodium CarbonateHCID 142176Phenyl triflimideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2724682Lithium diisopropylamideHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 22266210Tert-butyl 4-[(trifluoromethyl)sulfonyloxy]-1,2,5,6-tetrahydropyridinecarboxylate

Product 1

HCID 22266248tert-Butyl 4-[2-(trifluoromethyl)phenyl]-1,2,5,6-tetrahydropyridinecarboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Preparation A using 2-(trifluoromethyl)phenylboronic acid (Aldrich) (1.89 g, 10 mmol), tert-butyl 4-[(trifluoromethyl)sulfonyloxy]-1,2,5,6-tetrahydropyridinecarboxylate [prepared by the method of Wustrow, D. J. and Wise, L. D., Synthesis, 1991, 993-995, from tert-butyl-4-oxopiperidine-1-carboxylate (Aldrich), LDA (Aldrich) and N-phenyltrifluoromethanesulfonimide (Aldrich)] (3.64 g, 11 mmol), tetrakis(triphenylphosphine)palladium (0) (Strem Chemicals) (0.578 g, 0.5 mmol), LiCi (Aldrich) (1.27g, 30 mmol), and Na2CO3 (Aldrich) (2.46 g, 30 mmol) in water (15 mL) and DME (20 mL). Purification by silica gel chromatography (5:1 hexane:EtOAc) provided the title compound as a white foam (2.01 g). MS (ESI, pos. ion) m/z: 328 (M+1); MS (ESI, neg. ion) m/z: 326 (M−1). Calc'd for C17H20F3NO2: 327.34.

Workup

  1. customThe title compound was prepared
  2. customprepared by the method of Wustrow, D
  3. custom, Synthesis, 1991, 993-995
  4. customPurification by silica gel chromatography (5:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-62611c2b2fca4456a21b3f65b831c302
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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