Multi-step reaction with 8 steps
1: 1.) ammonium acetate, molecular sieves 3 Angstroem, 2.) methanolic HCl, NaBH3CN / 1.) methanol, 2 d, 2.) pH 3, r.t., 1 h
2: 84 percent / aq. NaHCO3 / toluene / 3 h / Ambient temperature
3: 82 percent / phosphate buffer, aq. NaOH / pig liver esterase / acetone / 7 h / 25 °C / pH 8
4: 83 percent / 4-dimethylaminopyridine, dicyclohexylcarbodiimide / CH2Cl2 / 1.) 0 deg C, 5 min, 2.) r.t., 3 h
5: 81 percent / aq. NaOH / methanol / 2.5 h / Ambient temperature
6: 67 percent / 2-isobutyloxy-1-isobutyloxycarbonyl-1,2-dihydroquinoline / tetrahydrofuran / 1.) r.t., 2.) reflux
7: 76 percent / CF3COOH / CH2Cl2 / 1.5 h / Ambient temperature
8: 30 percent / H2 / 10percent Pd-C / methanol / 20 °C
With
ammonium acetate; hydrogenchloride; dmap; sodium hydroxide; phosphate buffer; 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline; 3 A molecular sieve; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; trifluoroacetic acid;
palladium on activated charcoal; pig liver esterase;
In
tetrahydrofuran; methanol; dichloromethane; acetone; toluene;