Ethyl Acetate → HCID 86722343, compound

Participants

Reaction Steps

rac-(4aR,11bS)-11b-ethyl-1,2,4,4a,5,6,7,11b-octahydrospiro[dibenzo[a,c][7]annulene-3,2′-[1,3]dioxolan]-9-amine (22, R2=Ethyl) (0.345 g, 1.145 mmol) in THF (8 mL) was cooled to about 0° C. then NBS (0.204 g, 1.145 mmol) was added. After about 10 min, sat. aq. NaHCO3 (20 mL) and EtOAc (25 mL) were added. The mixture was warmed to rt and the layers were separated. The aqueous layer was extracted with EtOAc (15 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified on silica gel (12 g) using a gradient of 0-10% EtOAc in DCM. Product fractions were combined and concentrated under reduced pressure to yield rac-(4aR,11bS)-10-bromo-11b-ethyl-1,2,4,4a,5,6,7,11b-octahydrospiro[dibenzo[a,c][7]annulene-3,2′-[1,3]dioxolan]-9-amine (23, R2=Ethyl) (0.255 g, 59%); LC/MS, method 3, Rt=2.85 min, MS m/z 380, 382 (M+H)+. 1H NMR (400 MHz, DMSO) δ 7.03 (s, 1H), 6.55 (s, 1H), 5.04 (s, 2H), 3.89-3.73 (m, 4H), 2.80-2.73 (m, 1H), 2.58-2.46 (m, 1H), 2.26-2.19 (m, 1H), 2.14-2.05 (m, 1H), 2.02-1.88 (m, 2H), 1.72-1.45 (m, 4H), 1.43-1.18 (m, 5H), 0.60 (t, J=7.4 Hz, 3H).

Provenance & Evidence