Multi-step reaction with 9 steps
1.1: aluminum (III) chloride / 85.5 h / 2 - 25 °C / Inert atmosphere
1.2: 1.5 h / 0 - 10 °C / Inert atmosphere
2.1: sulfuric acid / 40 h / 82 - 83 °C / Inert atmosphere
3.1: potassium tert-butylate / dimethyl sulfoxide / 1.5 h / 20 - 25 °C / Inert atmosphere
3.2: 2.75 h / 20 - 25 °C / Inert atmosphere
4.1: zinc dibromide / toluene / 2 h / 22 - 30 °C
5.1: pyridoxal 5'-phosphate; isopropylamine / dimethyl sulfoxide / 47 h / 45 °C / pH 10.5 / Inert atmosphere; Enzymatic reaction
6.1: sodium tetrahydroborate / tetrahydrofuran / 1.33 h / 0 - 2 °C / Inert atmosphere
6.2: 17 h / 5 - 25 °C / Inert atmosphere
7.1: water; Isopropyl acetate / 2.08 h / 40 - 50 °C / Inert atmosphere
8.1: sodium hydroxide / water; tert-butyl methyl ether / 0.08 h / 20 - 25 °C / Inert atmosphere
8.2: 4.5 h / 24 °C / Inert atmosphere
9.1: copper(l) iodide; iron(III) chloride hexahydrate; potassium phosphate; 3,4,7,8-Tetramethyl-o-phenanthrolin / dimethyl sulfoxide / 24 h / 110 °C / Inert atmosphere
With
aluminum (III) chloride; sodium tetrahydroborate; potassium phosphate; copper(l) iodide; 3,4,7,8-Tetramethyl-o-phenanthrolin; iron(III) chloride hexahydrate; sulfuric acid; pyridoxal 5'-phosphate; potassium tert-butylate; isopropylamine; sodium hydroxide; zinc dibromide;
In
tetrahydrofuran; tert-butyl methyl ether; Isopropyl acetate; water; dimethyl sulfoxide; toluene;
DOI:10.1021/op400233z