Benzhydrylamine → 1-(Diphenylmethyl)azetidin-3-ol

Participants

Reaction Conditions

Reaction Steps

A solution of benzhydrylamine (200 ml, 1.16 mol) and epichlorohydrin (186 ml, 1 mol equiv) in methanol (600 ml) was stirred at room temperature for 5 days and then heated to 40° C. for 2 days. The solvent was then removed in vacuo, the residue dissolved in isopropyl alcohol (500 ml) and the solution heated under reflux for 6 hours. The solution was cooled to room temperature and the precipitate filtered off. The solid was partitioned between dichloromethane (400 ml) and saturated NaHCO3 solution (500 ml). The aqueous phase was extracted with dichloromethane (2×400 ml) and the combined organic phases dried over anhydrous MgSO4. The solvent was then removed in vacuo to give the title compound (86 g) as a crystalline solid.

Provenance & Evidence