Multi-step reaction with 8 steps
1: oxalyl chloride, DMF, pyridine / tetrahydrofuran; acetonitrile / 1 h / -30 °C
2: CuI, LiAlH3)3>3 / tetrahydrofuran; acetonitrile / 0.17 h / -78 °C
3: 78 percent / H2 / PtO2 / methanol / 0.5 h / 2585.7 Torr
4: 86 percent / Et3N, HgCl2 / dimethylformamide / 16 h / Ambient temperature
5: 82 percent / pyridinium chlorochromate / CH2Cl2 / 16 h / Ambient temperature
6: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF, 0 deg C, 0.5 h
7: 26 percent / NaBH4 / ethanol / 2 h / 0 °C
8: 51 percent / H2 / PtO2 / methanol / 2 h / 2585.7 Torr
With
pyridine; sodium tetrahydroborate; copper(l) iodide; oxalyl dichloride; hydrogen; sodium hydride; lithium tri-t-butoxyaluminum hydride; triethylamine; N,N-dimethyl-formamide; pyridinium chlorochromate; mercury dichloride;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm970479e