Multi-step reaction with 7 steps
1: 82 percent / NaNO2, Br2, 48percent HBr / 5 °C
2: 43 percent / Cu, HMPA / 112 - 130 °C / autoclave
3: 21 percent / KMnO4 / H2O / Heating
4: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min
5: 36 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature
6: propan-2-ol / 40 °C
7: dimethylformamide / 100 - 110 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; potassium permanganate; lithium aluminium tetrahydride; phosphoric acid; hydrogen bromide; bromine; chloroformic acid ethyl ester; copper; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; sodium nitrite;
In
water; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1248/cpb.38.2446