Ammonia → HCID 86586745, compound

Participants

Reaction Steps

(1R*,2R*,5S*,6R*)-8-Benzyl-2-{(1S*)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-carboxylic acid (Example 130; 4.82 g, 6.99 mmol), triethylamine (2.93 ml, 20.97 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (2.68 g, 13.98 mmol), 4-dimethylaminopyridine (10 mg), and ammonia in dioxane (41.94 ml, 20.97 mmol, 0.5M solution) were combined in dichloromethane (40 ml) and stirred in a sealed flask for 2 hours at room temperature. The reaction mixture was then diluted with water and the organics removed and the aqueous further extracted with dichloromethane (×2). All organics were combined, dried (MgSO4) and concentrated in vacuo to give a brown oil which was purified by flash column chromatography [3% methanol in dichloromethane] to give the title compound as a cream-coloured solid (1.76 g, 60%).

Provenance & Evidence