Hydroxylamine → HCID 57904851, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of benzyl 8-cyano-1,4-dioxaspiro[4.5]decan-8-ylcarbamate (37.4 g, 118.33 mmol), hydroxylamine (7.98 mL, 130 mmol, 50 wt % in water) in EtOH (750 mL) was heated at 70° C. for 48 h. The mixture was then cooled to room temperature and treated with diethyl acetylenedicarboxylate (22.73 mL, 142 mmol). After 48 h at room temperature, the reaction mixture was concentrated and the resulting yellow residue was taken up in ethyl acetate (500 mL), washed with water (2×100 mL) followed by brine (100 mL), then dried (Na2SO4), filtered and concentrated to give a yellow oil. Flash chromatography on silica gel (using 5% to 50% ethyl acetate-hexane gradient) afforded the title compound as a yellow oil (50 g, 82% yield). 1H NMR (500 MHz, CDCl3) δ: 7.33-7.37 (m, 5H), 5.80 (s, 1H), 5.07 (s, 2H), 4.84 (d, 1H, J=23.8 Hz), 4.33 (q, 1H, J=7.02 Hz), 4.27 (q, 1H, J=7.22 Hz), 4.09-4.20 (m, 3H), 3.93 (s, 2H), 3.90-3.92 (m, 2H), 2.16-2.23 (m, 4H), 2.03 (s, 1H), 1.62-1.74 (m, 4H), 1.24-1.37 (m, 6H). LCMS (M+H)=336.14.

Provenance & Evidence