Hydrochloric Acid → HCID 131730412, compound

Participants

Reaction Conditions

Reaction Steps

Trans-methyl 2-(3,5-dichlorophenyl)-4-(3-ethoxy-3-oxopropanoyl)piperidine-1-carboxylate (0.6 g, 1.49 mmol) (from example 55, step 1) was dissolved in MeOH (6.11 mL) and cooled to −40° C. under nitrogen. Sodium hydroxide (0.393 mL, 1.49 mmol) in water (0.611 mL) was added and the mixture stirred at −40° C. for 20 min. Hydroxylamine (50% by weight in water, 0.091 mL, 1.49 mmol) was added and stirring continued at −40° C. for 3.5 h. The reaction mixture was then transferred to a preheated 80° C. solution of 6 M hydrogen chloride (7.71 mL, 46.24 mmol) and heating was continued for 20 min. The solvent was then evaporated. DCM and water were added, shaken and the phases separated. The organic phase was dried with a phase separator and evaporated to yield crude trans-methyl 2-(3,5-dichlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (300 mg, 54%). MS m/z 371 (M+H)+

Provenance & Evidence