Ethyl Acetate → HCID 89077462, compound

Participants

Reaction Steps

Prepared in 72% yield (4.5 g, 14.5 mmol) from the reaction of 2-bromocyclohexanoyl bromide (4.53 g, 20.1 mmol) with O-benzylhydroxylamine, hydrochloride (3.21 g, 20.1 mmol) via general procedure A. Rf=0.47 (3:1; hexanes:EtOAc); mp=84.6-86.1° C.; 1H NMR (400 MHz, CDCl3) δ 8.98 (br s, 1H), 7.51-7.31 (m, 5H), 4.94 (s, 2H), 2.13 (ddd, J=14.6, 10.9, 4.0 Hz, 2H), 2.00 (dt, J=14.0, 4.1 Hz, 2H), 1.80-1.57 (m, 5H), 1.42-1.23 (m, 1H). 13C NMR (101 MHz, CDCl3) δ 169.6, 135.0, 129.6, 129.0, 128.7, 78.2, 38.1, 24.7, 22.6. IR (neat) 3235 (br), 3034, 2936, 2862, 1680, 1651 (s), 1470, 1459, 1270, 1249, 1210, 1122, 1025, 1000 cm-1; HR-APPIMS calculated for C14H16BrNO2 (M+H)+ 312.0594, observed 312.0206.

Provenance & Evidence