Lithium Hydroxide → HCID 66667042, compound

Participants

Reaction Steps

A solution of (R)-methyl 2-(1-(4-(3-(2-methylpyridin-4-yl)-3-oxo-1-o-tolylpropyl)-phenyl)piperidine-4-carboxamido)acetate (116 mg, 226 μmol) in tetrahydrofuran (3 mL), 1 M aq. lithium hydroxide solution (2.26 mL, 2.26 mmol) and methanol (1 mL) was stirred for 2 h at room temperature, then after addition of 1 M aq. potassium hydrogensulfate solution (2.5 mL) and sat. aq. ammonium chloride solution (5 mL) the reaction mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to produce [(1-{4-[(R)-3-(2-methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-phenyl}-piperidine-4-carbonyl)-amino]-acetic acid. This was reacted in analogy to example 132, step 6 with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to produce the title compound (42 mg, 36%). Yellow semisolid, MS (ESI+): m/z=515.6 ([M+H]+).

Provenance & Evidence