4-Methylmorpholine → (3R)-3-(4-Chlorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl 4-(nitrooxy)butanoate

Participants

Reaction Steps

N-Methylmorpholine (90 μL, 0.82 mmol) was added to a stirred solution of (R)-(−)-cicletanine (48 mg, 0.18 mmol), 4-(nitrooxy)butanoic acid (27 mg, 0.18 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (42 mg, 0.22 mmol), and 4-dimethylaminopyridine (9 mg, 0.07 mmol) in dichloromethane (1.8 mL). The solution was stirred overnight at room temperature. The mixture was concentrated under reduced pressure. The residue was purified by HPLC reverse phase (C-18) cluting with acetonitrile/water with 0.05% TFA to afford the title compound as a colorless oil. LC-MS: m/z 392.9 (M+H).

Provenance & Evidence