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

Participants

Reaction Steps

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.

Provenance & Evidence