Multi-step reaction with 10 steps
1: 1.) 15percent HCl; 2.) Ag2CO3 / 18 h / Ambient temperature
2: 60percent NaOH in oil / dimethylformamide / 16 h / Ambient temperature
3: 6N HCl / acetic acid / 22 h / 65 °C
4: 98 percent / NaBH4 / ethanol / 0.67 h / 0 °C
5: 81 percent / 4-dimethylaminopyridine, triethylamine / CH2Cl2 / 16 h / Ambient temperature
6: 93 percent / pyridine / 20 h / 0 °C
7: 83 percent / sodium azide, 15-crown-5 / hexamethylphosphoric acid triamide / 48 h / 80 - 90 °C
8: 96 percent / LiAlH4 / diethyl ether / 6.5 h / Ambient temperature
9: 72 percent / triethylamine / CH2Cl2 / 1 h / Ambient temperature
10: 72 percent / 42percent aq. HBF4, triethylamine / acetonitrile / Ambient temperature
With
pyridine; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; tetrafluoroboric acid; sodium azide; 15-crown-5; triethylamine; silver carbonate;
In
N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.3987/COM-95-7292