Multi-step reaction with 15 steps
1: hydrogen / Pd-C / ethanol / Ambient temperature
2: NaBH4 / methanol / 0 °C
3: pyridine / Ambient temperature
4: 10percent HCl / acetone / Ambient temperature
5: 1.) Br2, 2.) LiBr, Li2CO3 / 1.) CHCl3, room temperature, 2.) DMF, 125 deg C
6: NaNH2, liq. NH3 / -78 °C
7: p-TsOH / benzene / Heating
8: 5percent NaOH, MeOH / Ambient temperature
9: 1.) Na. liq NH3, 2.) 10percent HCl / 1.) -78 deg C, 2.) acetone, room temperature
10: 1.) pyridinium hydrobromide perbromide, 2.) LiBr, Li2CO3 / 1.) CHCl3, room temperature, 2.) DMF, 125 deg C
11: 30percent H2O2, 10percent NaOH / methanol / Ambient temperature
12: p-TsOH / CH2Cl2 / Ambient temperature
13: 1.) LiAlH4, 2.) pyridine / 1.) THF, room temperature, 2.) room temperature
14: 1.) NaH, 2.) p-TsOH / 1.) THF, reflux, 2.) room temperature
15: pyridine / Ambient temperature
With
pyridine; hydrogenchloride; methanol; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; ammonia; hydrogen; dihydrogen peroxide; bromine; pyridinium hydrobromide perbromide; sodium; lithium carbonate; sodium hydride; toluene-4-sulfonic acid; sodium amide; lithium bromide;
palladium on activated charcoal;
In
methanol; ethanol; dichloromethane; acetone; benzene;
DOI:10.1021/ja00400a078