Triethylamine → HCID 86591141, compound

Participants

Reaction Steps

The (+/−)-tert-butyl (3S,4S)-4-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-hydroxypiperidine-1-carboxylate (206 mg, 0.51 mmol), 1′-biphenyl-4-carbonyl chloride (540 mg, 2.50 mmol), triethylamine (400 mg, 4.00 mmol), and a catalytic amount of dimethylaminopyridine (10.0 mg, 0.08 mmol) was mixed together in acetonitrile (10.0 mL) at room temperature for 16 H. Ammonium hydroxide solution (5 mL) was added to the solution and it was stirred for 1 H. The heterogeneous solution was poured into ethyl acetate (50 mL) and hexanes (5 mL). The solution was extracted with 1N aqueous hydrochloric acid (2×10 mL), extracted with saturated aqueous sodium bicarbonate (2×10 mL), and extracted with saturated with saturated aqueous ammonium chloride (2×10 mL). The solution was dried over sodium sulfate and solvent removed at reduced pressure. The (+/−)-tert-butyl (3R,4R)-3-[(1,1′-biphenyl-4-ylcarbonyl)oxy]-4-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)piperidine-1-carboxylate (164 mg, 0.28 mmol) was isolated as a semisolid by radial silica gel chromatography (25% ethyl acetate/hexanes). HRMS m/z 588.3150 (calcd for M+H 588.3140.)

Provenance & Evidence