[CH:1]([N:14]1[CH2:17][C:16](=[O: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.[CH2:19]([Mg]I)[CH2:20][CH3:21].ICCC.[Mg].[Cl-].[NH4+]>C(OCC)C.O>[CH:1]([N:14]1[CH2:17][C:16]([OH:18])([CH2:19][CH2:20][CH3:21])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
A solution of 7.5 g of 1-benzhydryl-3-oxoazetidine dissolved in 50 cm3 of ethyl ether is added in the course of 20 minutes at between 0 and 5° C. to a solution of propylmagnesium iodide in ethyl ether, prepared under the usual conditions from 10.75 g of iodopropane and 1.55 g of magnesium in 75 cm3 of ethyl ether. The temperature is allowed to rise to approximately 20° C. and the mixture is stirred at the same temperature for 2 hours. After cooling to approximately 0° C., 50 cm3 of water and 50 cm3 of 10% aqueous ammonium chloride solution are added successively while the latter temperature is maintained. The aqueous phase is extracted with 3 times 50 cm3 of ethyl ether. The combined organic extracts are dried over magnesium sulphate and concentrated to dryness under reduced pressure (20 kPa) at approximately 30° C. The dry extract is chromatographed on 100 g of silica gel (0.04-0.063 mm) suspended in a cyclohexane mixture containing 20% of ethyl acetate. The desired product is eluted with 130 cm3 of the same solvent mixture. 8 g of 1-benzhydryl-3-hydroxy-3-propyl-azetidine are obtained in the form of a pale yellow oil, which is used without further purification for the subsequent steps.
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