Multi-step reaction with 11 steps
1: 1) NaH / 1) THF, mineral oil, 0 deg C, 2) THF, 30 min at r.t.
2: Et3N / 3 h / Ambient temperature
3: 73 percent / NaN3 / aq. ethanol / 8 h / Heating
4: 80 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h
5: Et3N / CH2Cl2 / 1.5 h / Ambient temperature
6: 75 percent / 1,2-dimethoxy-ethane / 0.5 h / Heating
7: 1) 55percent hydrazine hydrate, 2) conc. HCl / 1) MeOH, 2 h, reflux, 2) water, 1 h, reflux
8: 1) methanolic HCl, 2) sodium cyanoborohydride / 1) MeOH, 10 min, 2) 24 h, r.t.
9: 89 percent / Et3N, 1,3-propanedithiol / methanol / 48 h / Ambient temperature
10: 94 percent / Na, NH3(liq.) / 1,2-dimethoxy-ethane / 0.5 h / -42 °C
11: aq. NaHCO3 buffer / 6 h
With
1.3-propanedithiol; hydrogenchloride; sodium azide; NaHCO3 buffer; tetrabutyl ammonium fluoride; ammonia; sodium; sodium hydride; sodium cyanoborohydride; hydrazine hydrate; triethylamine;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane;
DOI:10.1021/jo00013a053