Ethylene Glycol → HCID 117857408, compound

Participants

Reaction Conditions

Reaction Steps

To Hydromorphone HCl (15.0 g, 46.7 mmol) was added ethylene glycol (80 mL) and methane sulfonic acid (10 mL) and the reaction heated at 80° C. overnight. The reaction was cooled to room temperature and poured into ice/NH3(aq) (˜350 mL). The product was extracted with dichloromethane and dried over MgSO4 before concentration under reduced pressure to give (4R,4aR,7aR,12bS)-3-methyl-1,2,3,4,4a,5,6,7a-octahydrospiro[4,12-methanobenzofuro[3,2-e]isoquinoline-7,2′-[1,3]dioxolan]-9-ol (19 g, 99.9% LCMS); [M+H]+330.5. This was taken onto the next step without purification.

Provenance & Evidence