1: ethanol 2: sodium hydroxide / water View Scheme

Chiralpak AD column in ethanol; hexane Resolution of racemateHPLC conditions; optical yield given as percent ee;

1: With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine in tetrahydrofuran; water; dimethyl sulfoxide T=0 - 8°C; 1.5 h; 2: With N-ethyl-N,N-diisopropylamine in methanol; acetonitrile T=60 - 63°C; 2.33333 h; 3: With ammonium chloride in methanol; water; ethyl acetate; acetonitrile T=25°C;

1: methylamine With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.833333 h; Inert atmosphere; 2: 6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N,N-diisopropyl-2-naphthamide in tetrahydrofuran; hexane T=0 - 20°C; 16 h; Inert atmosphere; 3: With water; sodium chloride in tetrahydrofuran; hexane Inert atmosphere;

1: 6-bromo-N-methyl-2-naphthamide With 2-(trifluoromethyl)phenyllithium in tetrahydrofuran; hexane T=-65 - -55°C; 0.833333 h; Inert atmosphere; 2: 5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one in tetrahydrofuran; hexane T=-65°C; 1.5 h; Inert atmosphere; 3: With water; ammonium chloride in tetrahydrofuran; hexane Inert atmosphere;

1: 6-bromo-N-methyl-2-naphthamide With n-butyllithium in tetrahydrofuran; hexane T=-65 - 10°C; 1 h; Cooling with acetone-dry ice; 2: 5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one in tetrahydrofuran; hexane 1.5 h;

methylamine in tetrahydrofuran; THF-ethyl acetate; water

ammonia in tetrahydrofuran

ammonia in tetrahydrofuran

1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere 2.1: 2-(trifluoromethyl)phenyllithium / tetrahydrofuran; hexane / 0.83 h / -65 - -55 °C / Inert atmosphere 2.2: 1.5 h / -65 °C / Inert atmosphere 2.3: Inert atmosphere View Scheme