Multi-step reaction with 17 steps
1: iron dust, 12 M HCl / methanol / 10 h / Heating
2: Na2CO3 / diethyl ether; H2O / 1.) 0 deg C, 30 min; 2.) room temp., 2 h
3: 93 percent / Jones reagent / acetone / 1.) 0 deg C, 30 min; 2.) room temp., 1 h
4: tetrahydrofuran / 2 h / Ambient temperature
5: 2 M aq. NaN3 / tetrahydrofuran; H2O / 2 h / Ambient temperature
6: toluene / 0.5 h / Heating
7: toluene / 2 h / 60 °C
8: 100 percent / hydrogen / 10percent Pd-C / ethanol / 2 h
9: acetonitrile / 1 h
10: NaBH3CN / acetonitrile / 12 h / 50 °C
11: 85 percent / molecular sieves 3 Angstroem / ethanol / 72 h / Heating
12: 75 percent / 1 M nBu4NF / tetrahydrofuran / 5 h / Ambient temperature
13: 5 M KOH / methanol / 3 h / Ambient temperature
14: DCC / tetrahydrofuran / Ambient temperature
15: BH3*SMe2 / tetrahydrofuran / 5 h / Ambient temperature
16: CAN / acetonitrile; H2O / 0.08 h
17: 78 percent / NaHCO3 / ethanol / 3 h / Ambient temperature
With
hydrogenchloride; potassium hydroxide; sodium azide; jones reagent; ammonium cerium(IV) nitrate; dimethylsulfide borane complex; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; iron; sodium cyanoborohydride; sodium hydrogencarbonate; sodium carbonate; dicyclohexyl-carbodiimide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; water; acetone; toluene; acetonitrile;
DOI:10.1016/S0040-4020(01)85065-1