Multi-step reaction with 15 steps
1: DIBAH / toluene / -78 °C
2: toluene / 60 °C
3: H2 / 10percent Pd/C / methanol / Ambient temperature
4: (COCl)2, DMSO, Et3N / CH2Cl2 / -78 °C
5: Zn, TiCl4 / Ambient temperature
6: 100 percent / Siam2BH / tetrahydrofuran / 0 °C
7: LiAlH4 / tetrahydrofuran / 0 °C
8: (COCl)2, DMSO, Et3N / CH2Cl2 / -78 °C
9: (PhCH2)2NH2(+)*TFA(-) / benzene / 60 °C
10: tBuOK / tetrahydrofuran / Ambient temperature
11: 9-BBN / tetrahydrofuran / 0 °C
12: 50percent aq. NaOH / Bu4N*HSO4 / CH2Cl2 / 40 °C
13: Bu4NF / tetrahydrofuran / Ambient temperature
14: SO3*Py, Et3N / dimethylsulfoxide / Ambient temperature
15: 90 percent / NaH / tetrahydrofuran / Ambient temperature
With
sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO3 complex; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; bis-(1,2-dimethylpropyl)borane; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; zinc; dibenzylammonium trifluoroacetate salt;
palladium on activated charcoal; tetra(n-butyl)ammonium hydrogensulfate;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; toluene; benzene;
DOI:10.1248/cpb.37.1647