4-(Trifluoromethyl)phenyl isocyanate → HCID 25252814, compound

Participants

Reaction Steps

A solution of (R)-tert-butyl 2-(4-(4-chlorobenzyl)isoxazol-5-yl)pyrrolidine-1-carboxylate (32 mg, 0.9 mmol) was dissolved in 4M HCl in 1,4-dioxane (2 mL), stirred for 2 h and then concentrated in vacuo. The resulting reaction residue was suspended in dicloromethane (2 mL) and DIEA (31 μL, 0.18 mmol) before 1-isocyanato-4-(trifluoromethyl)benzene (25 mg, 0.13 mmol) was added. After 16 h of stirring, the reaction mixture was concentrated in vacuo. Purification of the resulting residue by silica gel column chromatography (hexanes/ethyl acetate gradient, 10-100% EtOAc) afforded (R)-2-(4-(4-chlorobenzyl)isoxazol-5-yl)-N-(4-(trifluoromethyl)phenyl)pyrrolidine-1-carboxamide (19 mg, 47%).

Provenance & Evidence