Hydroxylamine → (2R,3S)-N,2-dihydroxy-3-{[4-(4-methoxyphenyl)piperazin-1-yl]carbonyl}-5-methylhexanamide

Participants

Reaction Steps

To a suspension of (5R)-5-((1S)-1-{[4-(4-methoxyphenyl)piperazin-1-yl]carbonyl}-3-methylbutyl)-2,2-dimethyl-1,3-dioxolan-4-one (108 mg, 0.27 mmol) in iPrOH (4 mL) was added a 50% aqueous solution of hydroxylamine (80 μL) and the resulting mixture was stirred at RT for 2 hours. Then the white solid was filtered off, washed with water and dried under reduced pressure to give 56 mg (55%) of the title compound as a white powder. HPLC, Rt: 1.57 min (purity: 99.1%). LC/MS, M+(ESI): 380.2, M−(ESI): 378.2. 1H NMR (CD3OD, 300 MHz) δ 7.01 (d, J=9.1 Hz, 2H), 6.89 (d, J=9.1 Hz, 2H), 4.05 (d, J=6.8 Hz, 1H), 3.96 (m, 2H), 3.80 (m, 1H), 3.78 (s, 3H), 3.68 (m, 1H), 3.49 (m, 1H), 3.15-2.99 (m, 4H), 1.72 (m, 1H), 1.54 (m, 1H), 1.29 (m, 1H), 0.96 (d, J=6.5 Hz, 3H), 0.95 (d, J=6.4 Hz, 3H).

Provenance & Evidence