[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:14][CH:13]3[N:15](C)[CH:10]([CH2:11][CH2:12]3)[CH:9]=2)=[CH:4][CH:3]=1.ClC(OC(Cl)C)=O.[C:24]([OH:30])(=[O:29])[CH2:25][C:26]([OH:28])=[O:27]>C(O)(C)C>[C:24]([OH:30])(=[O:29])[CH2:25][C:26]([OH:28])=[O:27].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:9][CH:10]3[NH:15][CH:13]([CH2:12][CH2:11]3)[CH:14]=2)=[CH:6][CH:7]=1The title compound was prepared from (±)-3-(4-fluorophenyl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene (1.6 g, 7.37 mmol) and 1-chloroethyl chloroformate (1.2 mL, 1.6g, 11 mmol). The free base of the title compound was dissolved in isopropanol and added malonic acid (0.43 g, 4.1 mmol), the title compound precipitated from this solution and was isolated by filtration. Yield 1.14 g (50%) m.p. 132.2-132.6° C.
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