18-Crown-6 → HCID 68081530, compound

Participants

Reaction Steps

A flask was purged with nitrogen and then charged with N-Boc-nortropine (1.64 g, 7.20 mmol), 18-crown-6 (1.59 g, 6.00 mmol), and anhydrous tetrahydrofuran (60 mL). Potassium tert-butoxide (1.34 g, 12.0 mmol) was added portion-wise, and the mixture was stirred vigorously under nitrogen for 1 hour. 4-(Bromomethyl)-5-cyclopropyl-3-(o-tolyl)isoxazole (1.75 g, 6.00 mmol) in tetrahydrofuran (20 mL, anhydrous) was added dropwise, and the reaction mixture was stirred for 1 hour under nitrogen. The solvent was reduced in vacuo and the mixture diluted with water (100 mL) and ethyl acetate (100 mL). The organic layer was separated, dried over magnesium sulfate, and evaporated in vacuo. The crude residue was purified by silica gel chromatography using a gradient of 0-100% ethyl acetate/hexanes to yield the desired product as a yellow oil. MS m/z 439.2 (M+1).

Provenance & Evidence