Reaction #74636

Reaction equation

1-(diphenylmethyl)azetidin-3-one

tert-butyl hydrazinecarboxylate

acetic acid

→

title compound

Yield 94.0%

tert-butyl 2-[1-(diphenylmethyl)azetidin-3-ylidene]hydrazinecarboxylate

Yield 94.0%

Solvents

methanol

Conditions

Workup

1. 1
   ConcentrationThen the reaction mixture was concentrated in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane (500 ml)
3. 3
   WashThe organic layer was washed with 1M aqueous sodium hydroxide solution (2×150 ml), water (3×150 ml), saturated aqueous sodium chloride solution (150 ml)
4. 4
   Dryingdried over anhydrous sodium sulphate
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe crude product was triturated with diethyl ether

Procedure

To a stirred solution of 1-(diphenylmethyl)azetidin-3-one (Preparation 693, 11.4 g, 48 mmol) and tert-butyl hydrazinecarboxylate (6.3 g, 48 mmol) in methanol (110 ml) at 0° C. was added acetic acid (5.56 ml, 96 mmol) dropwise and stirred at room temperature for 18 hours. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in dichloromethane (500 ml). The organic layer was washed with 1M aqueous sodium hydroxide solution (2×150 ml), water (3×150 ml), saturated aqueous sodium chloride solution (150 ml), dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product was triturated with diethyl ether to get 15.8 g (94%) of the title compound as a white solid.

Source