Multi-step reaction with 8 steps
1: 76.9 percent / pyridine / CH2Cl2 / 2 h / 0 °C
2: 77 percent / pyridine / 1,2-dichloro-ethane / 1) r.t., 5 h, 2) 70 deg C, 65 h
3: 96 percent / sodium azide / hexamethylphosphoric acid triamide / 2 h / 110 °C
4: 86.6 percent / 1 N NaOH / CHCl3; methanol / 0.25 h / Ambient temperature
5: 6.86 g / H2, triethylamine / 10percent Pd-C / methanol / 1.5 h / Ambient temperature
6: 72.1 percent / triethylamine / CH2Cl2; ethanol / 72 h / 4 °C
7: hydrogen, 30percent aq. trifluoroacetic acid / 10percent Pd-C / methanol / 16 h / 760 Torr / Ambient temperature
8: 46.2 percent / triethylamine / CH2Cl2 / 2.5 h / 0 °C
With
pyridine; sodium hydroxide; sodium azide; hydrogen; triethylamine; trifluoroacetic acid;
palladium on activated charcoal;
In
methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; chloroform; 1,2-dichloro-ethane;
DOI:10.1016/0008-6215(90)80086-I