Water → HCID 22601510, compound

Participants

Reaction Steps

A solution of (±)-8-ethoxycarbonyl-3-(4-methoxybenzo[b]thiophen-2-yl)-8-azabicyclo[3.2.1]oct-2-ene (0.719 g, 2.09 mmol), hydrazine hydrate (0.51 mL, 10.4 mmol) and KOH (0.700 g, 12.5 mmol) in ethylene glycol (15 mL) was heated at reflux in a sand bath for 3 h. The reaction mixture was then cooled to room temperature and stirred overnight. The reaction mixture was poured into water (20 mL). This mixture was extracted with Et2O (3×30 mL). The combined organic layers were washed with 1.0 N HCl (1×175 mL). The layers were separated and the aqueous layer was basified with 2.5 N NaOH (25 mL). This layer was extracted with EtOAc (2×275 mL). The combined organic layers were then dried over MgSO4, concentrated, and the residue was purified by medium pressure chromatography (silica gel, 7% (10% conc. NH4OH in MeOH)/CH2Cl2] to give the intermediate title compound as an orange semi-solid (0.574 g, quantitative yield). mp (oxalate) 204-207° C. IR (KBr) 3400 (br) cm−1. Ion Spray MS 272 (M+H)+; 255 (M-16)+(base peak).

Provenance & Evidence