[CH:1]([N:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C(Cl)(Cl)Cl.O.[CH2:31]=[C:32]1[O:36][C:34](=[O:35])[CH2:33]1>>[C:34]([O:18][CH:16]1[CH2:17][N:14]([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:15]1)(=[O:35])[CH2:33][C:32]([CH3:31])=[O:36]11.95 g (0.05 mole) of 1-benzhydryl-3-hydroxyazetidine and 0.5 ml of triethylamine were dissolved in 50 ml of chloroform 6.3 g (0.075 mole) of diketene were then added dropwise to the solution, after which the reaction mixture was stirred for 10 hours at room temperature, and then water was added to it. The reaction mixture was then stirred for 30 minutes. At the end of this time, the chloroform layer was separated and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The concentrate was subjected to silica gel column chromatography, and 15.07 g (93%) of 1-benzhydryl-3-azetidinyl acetoacetate were obtained, as a pale yellow oil, from the fractions eluted with a 9:1 by volume mixture of toluene and ethyl acetate.
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