Hydrazine hydrate (1:1) → 3-(Aminooxy)-1-(diphenylmethyl)azetidine

Participants

Reaction Steps

To a solution of 2-{[1-(diphenylmethyl)azetidin-3-yl]oxy}-1H-isoindole-1,3(2H)-dione (600 mg, 1.56 mmol; which may be prepared as described in Step 2) in ethanol (13.3 mL) was added hydrazine hydrate (100 μL, 2.06 mmol). The resulting mixture was heated to reflux for 2 h then concentrated under reduced pressure. The residue was taken up in dichloromethane/methanol mixture then filtered. The filtrate was concentrated and the residue purified on column chromatography (eluent: Dichloromethane/NH3 7N in MeOH, 2% to 5%) to give the title compound (307 mg, 77%) as a clear oil.

Provenance & Evidence