Multi-step reaction with 12 steps
1: ClSO3H / CH2Cl2 / 22 h / 20 °C
2: 1.56 g / aq. NH4OH / ethyl acetate / 2 h / 20 °C
3: 94 percent / aq. NaOH / methanol / 22 h / 20 °C
4: 98 percent / NaBH4; BF3*Et2O / tetrahydrofuran / 3 h / 20 °C
5: 71 percent / K2CO3 / dimethylsulfoxide / 1.5 h / 80 °C
6: 83 percent / 10-camphorsulfonic acid / CH2Cl2 / 1.5 h / 20 °C
7: NaH / 48 h / 110 °C
8: 395 mg / NaH / N,N-dimethyl-acetamide; tetrahydrofuran / 3 h / 20 °C
9: 87 percent / p-TsOH*H2O / methanol; tetrahydrofuran / 16 h / 20 °C
10: 88 percent / pyridine / 18 h / 20 °C
11: NBS; AIBN / CCl4 / 2 h / Heating
12: 106 mg / NaI / dimethylformamide / 3 h / 60 °C
With
pyridine; chlorosulfonic acid; ammonium hydroxide; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; sodium iodide;
In
tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl acetamide; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm000538f