Multi-step reaction with 7 steps
1: 2,2-dimethoxypropane, HCl / 1.) reflux, 4 h, 2.) room temperature, overnight
2: 17.8 g / hydrogen / palladium on carbon / H2O / 15 h / 775.7 Torr / Ambient temperature
3: 95 percent / diisopropylethylamine / tetrahydrofuran / 4 h / Ambient temperature
4: 84 percent / LiBH4 / tetrahydrofuran / 5 h
5: 97 percent / pyridine, 4-dimethylaminopyridine / 0.5 h / Heating
6: 82 percent / potassium dihydrogen phosphate, sodium hydroxide / acetonitrile; H2O / 108 h / Ambient temperature; pH 7.0, Aspergillus niger lipase presence, other biologically active material: wheat germ lipase
7: 91 percent / triethylamine / tetrahydrofuran / 4 h / -10 - -5 °C
With
pyridine; hydrogenchloride; dmap; sodium hydroxide; potassium dihydrogenphosphate; lithium borohydride; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; 2,2-dimethoxy-propane;
palladium on activated charcoal;
In
tetrahydrofuran; water; acetonitrile;
DOI:10.1021/jo9519569