Reaktion #74636

Reaktionsgleichung

1-(diphenylmethyl)azetidin-3-one

tert-butyl hydrazinecarboxylate

acetic acid

→

title compound

Ausbeute 94.0%

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

Ausbeute 94.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThen the reaction mixture was concentrated in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane (500 ml)
3. 3
   WaschenThe 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
   Trocknendried over anhydrous sodium sulphate
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe crude product was triturated with diethyl ether

Vorschrift

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.

Quelle