Multi-step reaction with 19 steps
1: 1.) BuLi, tetramethylethylene diamine / 1.) hexane, 0 deg C, 4 h, 2.) hexane, from -78 deg C to 23 deg C, 15 min
2: 1.) BuLi / 1.) THF, -30 deg C, 13 h
3: CH3SO3H / CH2Cl2 / 0 °C
4: 1.) NaH / 1.) DMF, 0 deg C, 5 min, 2.) DMF, 23 deg C, 40 min
5: 99 percent / piperidine, acetic acid / benzene / 18 h / 23 °C
6: 94 percent / Et3N, HCOOH, Pd(PPh3)4 / 4 h / 23 °C
7: (PhO)2P(O)N3, Et3N, 4 Angstroem molecular sieves / toluene / 2 h / 70 °C
8: 1 h / 23 °C
9: 97 percent / H2, Rh<(COD)-(R,R)-DIPAMP>(+)*BF4(-) / 16 h / 23 °C / 2280 Torr
10: BF3*Et2O, H2O / CH2Cl2 / 0.17 h / 0 °C
11: BF3*Et2O, 4 Angstroem molecular sieves / CH2Cl2 / 18 h / 23 °C
12: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 6 h / 23 °C / 760 Torr
13: 61 percent / HOAc / 18 h / 23 °C
14: 87 percent / Cs2CO3 / dimethylformamide / 1 h / 23 °C
15: diisobutylaluminum hydride / toluene / 5 h / -78 °C
16: KF*2H2O / methanol / 0.33 h / 23 °C
17: CH3SO3H, 3 Angstroem molecular sieves / CH2Cl2 / 5 h / 23 °C
18: 72 percent / Et3N, DMAP / CH2Cl2 / 6 h / 23 °C
19: 89 percent / DMAP / CH2Cl2 / 13 h / 23 °C
With
piperidine; dmap; potassium fluoride; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; formic acid; methanesulfonic acid; N,N,N,N,-tetramethylethylenediamine; Rh<(COD)-(R,R)-DIPAMP>(+)*BF4(-); 3 A molecular sieve; 4 A molecular sieve; diphenyl phosphoryl azide; boron trifluoride diethyl etherate; water; hydrogen; sodium hydride; diisobutylaluminium hydride; caesium carbonate; acetic acid; triethylamine;
palladium on activated charcoal;
In
methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ja962480t