Ammonium Chloride → HCID 12859200, compound

Participants

Reaction Conditions

Reaction Steps

2-Carbomethoxy-3-phenyl-1,3-diazabicyclo-[3,3,0]octane prepared from 181 mg of (S)-2-(anilinomethyl)pyrrolidine was dissolved in 5.5 ml of THF, then admixed with 108 mg of anhydrous magnesium chloride, and heated and refluxed for 10 minutes. To the mixture cooled to -70° C., was added dropwise 1.38 equivalents of phenylmagnesium bromide dissolved in ether. After having been stirred at -70° C. for 15 minutes, the reaction mixture was admixed with saturated aqueous ammonium chloride solution and ether, and brought to room temperature. The mixture was extracted with ether and the ether layer was washed with 1 N aqueous sodium hydroxide solution and then with saturated aqueous sodium chloride solution. After drying, the ether layer was freed from the solvent by distillation under reduced pressure. The oily residue was purified by alumina column chromatography to obtain 230 mg (77%) of 2-benzoyl-3-phenyl-1,3-diazabicyclo[3,3,0]octane. NMR peaks: δ (ppm)=1.6-2.2 (4H, multiplet), 2.4-3.9 (5H, multiplet), 5.4 (1H, singlet), 6.1-7.9 (10H, multiplet).

Provenance & Evidence