Hydrochloric Acid → HCID 131730386, compound

Participants

Reaction Conditions

Reaction Steps

Trans-methyl 2-(4-chlorophenyl)-4-(3-ethoxy-3-oxopropanoyl)piperidine-1-carboxylate (184 mg, 0.50 mmol) (from example 27, step 1) was dissolved in MeOH (2 mL) and cooled to −40° C. under nitrogen. Sodium hydroxide (0.147 mL, 0.50 mmol) was added during 10 min and the yellow solution continued to stir at −40° C. for 20 min. Hydroxylamine (50% by weight in water, 0.031 mL, 0.50 mmol) was added during 8 min. The resulting solution was stirred at −40° C. for 3 h. The mixture was then rapidly poured into a prewarmed (80° C.) solution of 6 M hydrogen chloride (2.58 mL, 15.46 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 2-(4-chlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (155 mg, 92%) as a slightly yellow oil. MS m/z 337 (M+H)+

Provenance & Evidence