18-Crown-6 → Tert-butyl 3-((5-cyclopropyl-3-(2-phenylcyclopropyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octane-8-carboxylate

Participants

Reaction Steps

A solution of N-Boc-nortropine (80 mg, 0.35 mmol) and 18-crown-6 (125 mg, 0.5 mmol) in THF (2.5 mL) was cooled to 0° C., treated with potassium tert-butoxide (59 mg, 0.53 mmol) and stirred for 10 min. A solution of 4-(chloromethyl)-5-cyclopropyl-3-(2-phenylcyclopropyl)isoxazole (80 mg, 0.29 mmol) in THF (0.5 mL) was added and the resulting mixture stirred at rt for 2 h and then poured into water and extracted with EtOAc. The organic layer was collected, washed with brine, dried over Na2SO4, filtered, concentrated to yield tert-butyl 3-((5-cyclopropyl-3-(2-phenylcyclopropyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octane-8-carboxylate. MS m/z 409.1 (M−56+1).

Provenance & Evidence