[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]23[CH2:15][CH:14]2[C:13](=O)[NH:12][C:11]3=O)=[CH:6][CH:5]=1)[CH3:3].Cl.[OH-].[Na+]>O1CCCC1>[NH3:12].[CH3:3][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]23[CH2:15][CH:14]2[CH2:13][NH:12][CH2:11]3)=[CH:8][CH:9]=1)[CH3:1]
To a solution of 1-[4-(1-methylethyl)phenyl]-3-azabicyclo[3.1.0]hexane-2,4-dione (P20, 1.5 g) in anhydrous tetrahydrofuran (45 mL), BH3 in tetrahydrofuran (1 M, 26 mL) was added at 0° C. The reaction mixture was stirred at 65° C. for 6 hours, then cooled to 0° C., 6N aqueous HCl was added and the mixture was refluxed for 3 hours. The mixture was then basified with 5N aqueous NaOH and extracted with diethyl ether, the organic layer was washed with saturated aqueous NaCl and dried over Na2SO4. The solution was filtered and the filtrate was concentrated in vacuo. The crude compound was purified by a SCX cartridge (strong cationic exchanger, 10 g) eluting with MeOH (150 mL) and then NH3 0.3M in MeOH (100 mL) to give the title compound as colourless oil (0.5 g).
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