Hydroxyamine hydrochloride → HCID 58374065, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (S)-ethyl 1-(2-(4-cyanophenyl)-2-oxoethyl)piperidine-3-carboxylate, hydrobromide (100 mg, 0.262 mmol) in THF (2 mL) was added methylmagnesium bromide (0.350 mL, 1.049 mmol). After 1 hour, the reaction was quenched with water. The reaction mixture was diluted with ethyl acetate and washed with saturated NaCl. The organic layer was dried with MgSO4, filtered, and concentrated. The crude residue was dissolved in 2-propanol (10 mL). Sodium bicarbonate (88 mg, 1.049 mmol) and hydroxylamine hydrochloride (36.5 mg, 0.525 mmol) were added and the reaction was heated at 85° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with saturated NaCl. The organic layer was dried with MgSO4, filtered, and concentrated to yield 72 mg of (3S)-ethyl 1-(2-hydroxy-2-(4-((Z)-N′-hydroxycarbamimidoyl)phenyl)propyl)piperidine-3-carboxylate. MS (m+1)=350. HPLC Peak RT=0.11 minutes (Analytical Method B).

Provenance & Evidence