Multi-step reaction with 14 steps
1: 56 percent / DMAP; ethyldimethylaminopropyl carbodiimide / CH2Cl2 / 20 °C
2: 74 percent / NaBH4; AcOH / CH2Cl2
3: toluene / 15 h / 100 °C
4: 246 mg / toluene / 20 h / Heating
5: 56 percent / LiAlH4 / tetrahydrofuran / 0 °C
6: Et3N / CH2Cl2 / 0.75 h / 20 °C
7: 584 mg / NaN3 / dimethylsulfoxide / 3 h / 70 °C
8: aq. TFA / CH2Cl2 / 1 h
9: 75 percent / HOAt; 4-methylmorpholine; ethyldimethylaminopropyl carbodiimide / dimethylformamide / 1.25 h
10: aq. TFA / CH2Cl2 / 1 h
11: 85 percent / 1H-benzotriazole; 4-methylmorpholine; ethyldimethylaminopropyl carbodiimide / dimethylformamide / 1 h
12: H2; pyridine / Pd/C / methanol / 5 h
13: HgCl2; Et3N / dimethylformamide / 1 h / 0 °C
14: TFA; anisole / CH2Cl2 / 3 h
With
4-methyl-morpholine; pyridine; dmap; 1,2,3-Benzotriazole; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; 1-hydroxy-7-aza-benzotriazole; hydrogen; acetic acid; methoxybenzene; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; mercury dichloride;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm060384p