Sodium Carbonate → tert-Butyl 4-(2-acetylphenyl)-1,2,5,6-tetrahydropyridinecarboxylate

HRID 489673Notes

Reaction equation

HRID 489673 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1B(O)O)(=[O:3])[CH3:2].FC(F)(F)S(O[C:19]1[CH2:24][CH2:23][NH:22][CH:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:20]=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.[Li+].[Cl-].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>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:19]1[CH2:24][CH2:23][NH:22][CH:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:20]=1)(=[O:3])[CH3:2]

Participants

11

Reactant 7

HCID 10340Sodium CarbonateHCID 142176Phenyl triflimideHCID 433294Lithium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2724682Lithium diisopropylamideHCID 27343092-Acetylphenylboronic acidHCID 22266210Tert-butyl 4-[(trifluoromethyl)sulfonyloxy]-1,2,5,6-tetrahydropyridinecarboxylate

Product 1

HCID 22266253tert-Butyl 4-(2-acetylphenyl)-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-acetylphenylboronic acid (Aldrich) (1.63 g, 10 mmol), tert-butyl 4-[(trifluoromethyl)sulfonyloxy]-1,2,5,6-tetrahydropyridinecarboxylate [prepared by the method of Wustrow, D. J. and Wise, I. D. Synthesis, 1991, 993-995, from tert-butyl-4-oxopiperidine-1-carboxylate (Aldrich), LDA (Aldrich) and N-phenyltrifluoromethane-sulfonimide (Aldrich)) (3.64 g, 11 mmol), tetrakis(triphenylphosphine)palladium (0) (Strem Chemicals) (0.578 g, 0.5 mmol), LiCl (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 (1.77 g). MS (ESI, pos. ion) m/z: 302 (M+1); MS (ESI, neg. ion) m/z: 300 (M−1). Calc'd for C18H23NO3: 301.38.

Workup

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

Sources & evidence

ORD record
ord-b4b1af8f0f534756a53286a2d8450290
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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