Multi-step reaction with 7 steps
1: 1) CuCN / 1) THF, ether, cyclohexane, -70 deg C, 1 h, 2) THF, a) -65 deg C,, 1 h, b) -30 deg C, 2.5 h
2: 1) trifluoroacetic anhydride, 2,6-lutidine, 2) tetramethylguanidinium azide / 1) CH2Cl2, -78 deg C, 2) CH2Cl2, a) 0 deg C, 4 h, b) r.t., overnight
3: CF3COOH, H2O / 3 h / 0 - 20 °C
4: H2 / 10percent Pd/C / ethyl acetate / 20 °C / 1 Torr
5: 70 percent / Et3N / CH2Cl2 / 3 h / -20 °C
6: 80 percent / RuCl3*6H2O, NaIO4 / H2O; acetonitrile; CCl4 / 2.5 h / 20 °C
7: diethyl ether; methanol / 0.17 h
With
2,6-dimethylpyridine; ruthenium trichloride; sodium periodate; water; hydrogen; triethylamine; tetramethylguanidinum azide; trifluoroacetic acid; trifluoroacetic anhydride;
palladium on activated charcoal;
In
methanol; tetrachloromethane; diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile;