反应详情

A mixture of (1R*,2R*,5S*,6RS*)-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]octane (Example 81), trifluoroacetic acid (4 ml) and dichloromethane (6 ml) was stirred at room temperature overnight and concentrated in vacuo. The residue was treated with acetic hydrazide (164 mg, 2.21 mmol), triethylamine (0.5 ml, 3.6 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (350 mg, 1.8 mmol), and 4-N,N-dimethylaminopyridine (47 mg, 0.38 mmol). The mixture was stirred for 5 hours, quenched with saturated aqueous NaHCO3 and extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate) to give the title compound (180 mg, 50%).

1. concentrationconcentrated in vacuo
2. stirringThe mixture was stirred for 5 hours
3. customquenched with saturated aqueous NaHCO3
4. extractionextracted into dichloromethane
5. dry with materialThe combined organic extracts were dried (Na2SO4)
6. concentrationconcentrated
7. customThe residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate)