[C:1]1([CH:7]([N:9]2[CH2:12][CH:11](O)[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:14]#[N:15].[K+].CO.[C:19]([OH:26])(=[O:25])/[CH:20]=[CH:21]\[C:22]([OH:24])=[O:23]>CC(O)C>[C:19]([OH:26])(=[O:25])/[CH:20]=[CH:21]\[C:22]([OH:24])=[O:23].[C:1]1([CH:7]([N:9]2[CH2:12][CH:11]([C:14]#[N:15])[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1A slurry of methanesulfonate ester of 1-(1-phenylethyl)azetidin-3-ol (60.4 g, 223 mmol), potassium cyanide (43.5 g, 669 mmol) and methanol (350 mol) were allowed to stir at ambient temperature for 72 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was partitioned between 300 mL of an aqueous 20% potassium carbonate solution and 400 mL of diethyl ether. The organic layer was separated, dried (MgSO4) and concentrated in vacuo. The residue was chromatographed (SiO2, flash, ethyl acetate/hexane 1:3) to give 25.1 g (56%). A 1-g portion was dissolved in 2-propanol and treated with maleic acid (0.75 g, 6.5 mmol). The resulting solid was recrystallized from 2-propanol to give a white solid, mp 147°-148° C.
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