Multi-step reaction with 10 steps
1: 72 percent / HCl, H2 / 5percent Pd/C / methanol / 5 h / Ambient temperature
2: 98 percent / p-toluenesulfonic acid / 10 h / Heating
3: 1.) O3, 2.) LiOH / 1.) CH2Cl2, -78 deg C, 30 min, 2.) THF, RT, 2 h
4: 73 percent / camphorsulfonic acid / benzene / 2 h / Heating
5: 72 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
6: 93 percent / 4-(dimethylamino)pyridine, pyridine / 5 h / Ambient temperature
7: 95 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating
8: 95 percent / HCl / acetone / 6 h / Ambient temperature
9: 2.) NaH / 1.) ether, RT, 1 h, 2.) THF, reflux, 12 h
10: 1.) BH3*SMe2, 2.) aq. NaOH, H2O2 / 1.) 0 deg C - RT, 1.5 h, 2.) a) ) deg C, 30 min, b) 50 deg C, 1 h
With
pyridine; hydrogenchloride; dmap; lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; dimethylsulfide borane complex; camphor-10-sulfonic acid; hydrogen; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; ozone;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; acetone; benzene;
DOI:10.1021/jo00376a049