Reaktion #969892

Reaktionsgleichung

hydrochloric acid

ethyl 2-bromoisobutyrate

2-adamantylamine

benzaldehyde

→

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

Ausbeute 64.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe 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
   Extraktionextracted with ethyl acetate
5. 5
   TrocknenThe organic layer was dried with anhydrous sodium sulfate
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe obtained residue was purified

Vorschrift

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.

Quelle