Multi-step reaction with 15 steps
1: 76 percent / sodium, dimethyl sulfate / ethanol / 4 h / Ambient temperature
2: sodium hydroxide / H2O / 1.17 h / Heating
3: H2O / 2 h / 100 °C
4: thionyl chloride / 1 h., room temp. then 3 h., 60 deg C
5: 88.7 percent / HCl / ethanol / 48 h / Heating
6: 90 percent / NaHCO3 / dioxane; H2O / 40 h / 40 - 45 °C
7: 98 percent / LiBH4 / tetrahydrofuran / 3 h / Ambient temperature
8: 89 percent / H2 / 10percent Pd-C / ethyl acetate; H2O / 2 h / 760 Torr / Ambient temperature
9: 35 percent / CHCl3 / reflux, 18 h. then NaBH3CN, room temp., 8 h.
10: 2N KOH / methanol; H2O / 24 h / Ambient temperature
11: dicyclohexylcarbodiimide / acetonitrile / 1 h / Ambient temperature
12: 67 percent / trifluoroacetic acid / CH2Cl2 / 1 h / 0 °C
13: 62 percent / NaHCO3 / methanol / 60 h / Heating
14: 87 percent / pyridine / 18 h / Ambient temperature
15: 1.) NaH; 2.) 2N KOH / 1.) THF, 18 h., room temp.; 2.) 3 h.
With
hydrogenchloride; potassium hydroxide; sodium hydroxide; lithium borohydride; thionyl chloride; hydrogen; sodium; sodium hydride; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; dimethyl sulfate; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; dichloromethane; chloroform; water; ethyl acetate; acetonitrile;
DOI:10.1016/S0040-4020(01)96073-9