Multi-step reaction with 10 steps
1: 76 percent / Et3N / tetrahydrofuran / 36 h / Heating
2: 95 percent / CF3COOH / CH2Cl2 / 2 h / Ambient temperature
3: LiCl / tetrahydrofuran / 240 h / Ambient temperature
4: 77 percent / H2 / Raney-Ni / ethanol; aq. NH3 / 3040 Torr / Ambient temperature
5: 80 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 4 h / Ambient temperature
6: 63 percent / (EtO)2POCN, Et3N / dimethylformamide / 24 h / Ambient temperature
7: 76 percent / Et3N / dioxane / 29 h / 80 °C
8: 77 percent / camphorsulfonic acid, 4 Angstroem molecular sieve / methanol / 24 h / Ambient temperature
9: 1.) NaIO4; 2.) NaBH4 / 1.) MeOH, H2O, 0 deg C, 90 min; 2.) r.t., 60 min
10: Ph3P, CCl4 / tetrahydrofuran / 2 h / Heating
With
tetrachloromethane; lithium hydroxide; sodium tetrahydroborate; sodium periodate; diethyl cyanophosphonate; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium chloride;
nickel;
In
tetrahydrofuran; 1,4-dioxane; methanol; ammonium hydroxide; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/hlca.19980810541