Reacción #969892

Ecuación de reacción

hydrochloric acid

ethyl 2-bromoisobutyrate

2-adamantylamine

benzaldehyde

→

1-(adamantan-2-yl)-3,3-dimethyl-4-phenylazetidin-2-one

Rendimiento 64.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction solution was concentrated in vacuo
2. 2
   workup.DISSOLUTIONThe obtained residue was dissolved in toluene (5 mL)
3. 3
   workup.STIRRINGThe reaction solution was stirred at 130° C. for 5 hours
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   SecadoThe organic layer was dried with anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe obtained residue was purified

Procedimiento

A solution of 2-adamantylamine (50.0 mg, 0.330 mmol) in ethanol (2 mL) was added with benzaldehyde (56.3 mg, 0.330 mmol) at room temperature, and the resultant was stirred at the same temperature for 1.5 hours. The reaction solution was concentrated in vacuo. The obtained residue was dissolved in toluene (5 mL), and sequentially added with ethyl 2-bromoisobutyrate (109 mg, 0.660 mmol) and zinc (432 mg, 6.60 mmol) at room temperature. The reaction solution was stirred at 130° C. for 5 hours, and added with hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using preparative thin-layer chromatography (hexane:ethyl acetate=3:1), and 1-(adamantan-2-yl)-3,3-dimethyl-4-phenylazetidin-2-one (65.4 mg, 64.0%) was obtained as a white crystalline powder.

Fuente