Hydrochloric Acid → HCID 131730400, compound

Participants

Reaction Conditions

Reaction Steps

Trans-methyl 4-(3-ethoxy-3-oxopropanoyl)-2-(6-(trifluoromethyl)pyridin-3-yl)piperidine-1-carboxylate (70 mg, 0.17 mmol) (from example 40, step 1) was dissolved in MeOH (1 mL) and cooled to −45° C. under nitrogen. Sodium hydroxide (0.051 mL, 0.17 mmol) was added during 10 min and the yellow solution continued to stir at −45° C. for 20 min. Hydroxylamine (50% by weight in water, 10.66 μL, 0.17 mmol) was added during 8 min. The resulting solution was stirred at −45° C. for 3 h. The mixture was then rapidly poured into a prewarmed (80° C.) solution of 6 M hydrogen chloride (0.896 mL, 5.38 mmol) and the mixture continued to stir at 80° C. for 20 min. The solvent was evaporated and DCM/water added. The phases were separated and the organic phase passed through a phase separator and evaporated to yield crude trans-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)piperidine-1-carboxylate (60 mg, quant.) as a slightly yellow oil. MS m/z 372 (M+H)+

Provenance & Evidence