Multi-step reaction with 8 steps
1: Pd(Ph3P)4, piperidine / 2 h / 80 °C
2: H2 / Pd/CaCO3 / ethanol / 3 h / 2327.2 Torr
3: CrO3, H2SO4 / acetone / 0.25 h / Ambient temperature
4: diethyl ether
5: 1.) lithium hexamethyldisilazane, 2.) 2,4,6-triisopropylbenzenesulfonyl azide / 1.) THF, -78 deg C, 15 min, 2.) THF, from -78 to 0 deg C
6: H2 / Pd/CaCO3 / ethanol / 1 h / 2327.2 Torr
7: 1.) (i-Pr)2NEt, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate / 1.) DMF, RT, 2 min, 2.) DMF, RT, overnight
8: aq. NaOH / methanol / 1 h / Ambient temperature
With
piperidine; chromium(VI) oxide; sodium hydroxide; tetrakis(triphenylphosphine) palladium(0); sulfuric acid; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane;
Lindlar's catalyst;
In
methanol; diethyl ether; ethanol; acetone;
DOI:10.1021/jm970482y