Hydrochloric Acid → HCID 86585359, compound

Participants

Reaction Conditions

Reaction Steps

A solution of KOH (0.16 g, 2.8 mmol) in H2O (10 mL) was added to a solution of tert-butyl (5aS*,10bS*)-9,10-dichloro-6-(2-ethoxy-2-oxoethyl)-1,4,5,5a,6,10b-hexahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.96 g, 2.17 mmol) in THF (15 mL). The mixture was heated at 60° C. for 2 h. The reaction was then cooled to rt, acidified with 10% aqueous HCl, and extracted with EtOAc (3×30 mL). The combined organic extracts were washed with brine, dried over Na2SO4, decanted, and concentrated to give crude white foam (0.90 g): 1H NMR (300 MHz, CDCl3) δ 67.14 (d, J=8.3 Hz, 1H), 6.21 (d, J=8.4Hz, 1H), 4.08 (m, 1H), 3.93 (d, J=18.3 Hz, 1H), 3.76 (d, J=18.3 Hz, 1H), 3.47 (m, 5H), 2.04 (m, 4H), 1.44 (s, 9H); HRMS (FAB) calcd for C19H24CL2N2O4+H 415.1191, found 415.1198.

Provenance & Evidence