Hydroxyamine hydrochloride → ethyl 2-[(3S)-1-[(2R)-2-hydroxy-2-[4-[(Z)-N'-hydroxycarbamimidoyl]phenyl]ethyl]piperidin-3-yl]acetate

Participants

Reaction Conditions

Reaction Steps

To a mixture of ethyl 2-((R)-1-((S)-2-(tert-butyldimethylsilyloxy)-2-(4-cyanophenyl)ethyl)piperidin-3-yl)acetate (940 mg, 2.183 mmol) and sodium bicarbonate (733 mg, 8.73 mmol) in 2-propanol (50 mL) was added hydroxylamine hydrochloride (303 mg, 4.37 mmol). The reaction mixture was heated at 75° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with saturated NaCl. The organic layer was dried MgSO4, filtered, and concentrated to yield 920 mg of ethyl 2-((S)-1-((R)-2-hydroxy-2-(4-((Z)—N′-hydroxycarbamimidoyl)phenyl)ethyl)piperidin-3-yl)acetate. (M+H)=464; HPLC RT=1.57 minutes. 1H NMR (400 MHz, CDCl3) δ ppm 9.48 (1H, s), 7.55 (2H, d), 7.24 (2H, d), 5.68 (1H, s), 4.74 (1H, m), 4.00 (2H, q), 2.73 (1H, m), 2.65 (1H, m), 2.38 (1H, dd), 2.20 (1H, dd), 2.13 (2H, t), 2.00 (1H, m), 1.80 (3H, m), 1.58 (1H, m), 1.48 (1H, m), 1.38 (1H, m), 1.13 (3H, t), 1.0 (1H, m), 0.85 (9H, s), 0.00 (3H, s), −0.15 (3H, s).

Provenance & Evidence