Multi-step reaction with 8 steps
1: 1.) Mg / 1.) THF, RT, 1 h, 2.) THF, RT, 0.5 h
2: 100 percent / NaBH4 / methanol / 1 h / Ambient temperature
3: 1.) MsCl, Et3N, 2.) NaN3 / 1.) CH2Cl2, -5 to 0 deg C, 30 min, 2.) DMF, a) RT, 30 min, b) 40 deg C, 30 min
4: 94 percent / aq. HCl / tetrahydrofuran / 1 h / Ambient temperature
5: 1.) tert-BuOK / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 1 h
6: 97 percent / K2CO3 / dimethylformamide / 1 h / Ambient temperature
7: 76 percent / H2 / 5percent Pd/C / methanol / 10 h / 2280 Torr
8: 97 percent / Et3N / CH2Cl2 / Ambient temperature
With
hydrogenchloride; sodium tetrahydroborate; sodium azide; potassium tert-butylate; hydrogen; potassium carbonate; magnesium; methanesulfonyl chloride; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.44.765