Multi-step reaction with 12 steps
1: 94 percent / pyridine / 8 h / 20 °C
2: 83 percent / KNO3; TFAA / CHCl3 / 48 h / 0 °C
3: 93 percent / K2CO3 / methanol; H2O / 0.5 h
4: 73 percent / imidazole / dimethylformamide / 4 h / 20 °C
5: 89 percent / PPh3; DEAD / tetrahydrofuran / 1.5 h
6: 100 percent / NH2NH2*H2O / ethanol / 3 h / Heating
7: 84 percent / NaBH3CN; AcOH / methanol / 0 - 20 °C
8: 74 percent / NMM; isobutyl chloroformate / CH2Cl2 / 12 h / 20 °C
9: H2 / 10percent Pd/C / propan-1-ol / 4 h / 760.05 Torr
10: 3.732 g / Et3N / CH2Cl2 / 12 h / 20 °C
11: 89 percent / K2CO3 / methanol; H2O / 1.5 h
12: 94 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -50 - 20 °C
With
4-methyl-morpholine; 1H-imidazole; oxalyl dichloride; hydrogen; sodium cyanoborohydride; potassium carbonate; hydrazine hydrate; acetic acid; dimethyl sulfoxide; potassium nitrate; triethylamine; triphenylphosphine; trifluoroacetic anhydride; diethylazodicarboxylate; isobutyl chloroformate;
10percent Pd/C;
In
tetrahydrofuran; pyridine; methanol; propan-1-ol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide;
5: Mitsunobu reaction / 12: Swern oxidation;
DOI:10.1021/jo015512q