[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([C:7]23[CH2:12][CH:11]2[CH2:10][NH:9][C:8]3=O)=[CH:3][CH:2]=1.[CH3:15][Li].[BH4-].[Na+].[ClH:19]>CCOCC.CO>[ClH:19].[CH3:15][CH:8]1[NH:9][CH2:10][CH:11]2[C:7]1([C:4]1[CH:5]=[CH:6][C:1]([CH3:14])=[CH:2][CH:3]=1)[CH2:12]2Using the method of M. Takeda, et al., Chem. Pharm. Bull., 24, 2312 (1976), 1-(p-tolyl)-3-azabicyclo[3.1.0]hexan-2-one is reacted with methyllithium followed by sodium borohydride. Excess reagents are decomposed with methanol, followed by 1 N hydrochloric acid, and then 1 N sodium hydroxide and then evaporation of the solution gives a residue which is dissolved in ether. This solution is dried over sodium sulfate and filtered, and to the filtrate is added dry hydrogen chloride. Filtration of this suspension gives 2-methyl-1-(p-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride.
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