Reaction #969892

Reaction equation

hydrochloric acid

ethyl 2-bromoisobutyrate

2-adamantylamine

benzaldehyde

→

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

Yield 64.0%

Solvents

ethanol

Conditions

Workup

1. 1
   ConcentrationThe 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
   Extractionextracted with ethyl acetate
5. 5
   DryingThe organic layer was dried with anhydrous sodium sulfate
6. 6
   Concentrationconcentrated in vacuo
7. 7
   OtherThe obtained residue was purified

Procedure

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.

Source