Multi-step reaction with 9 steps
1.1: 76 percent / dibasic sodium phosphate; crushed urea; m-cloroperoxybenzoic acid / acetonitrile / 2 h / Heating
2.1: 95 percent / Triton B / methanol; 2-methyl-propan-2-ol / 48 h / 20 °C
3.1: 84 percent / NaBH4 / dioxane; H2O / 24 h / 20 °C
4.1: 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 1 h / 0 °C
5.1: 1.03 g / sodium iodide; NaHCO3 / acetone / 24 h / 20 °C
6.1: tert-butyllithium; hexamethylphosphoramide / tetrahydrofuran / 0.33 h / -78 °C
6.2: 99 percent / tetrahydrofuran / 0.67 h / -78 °C
7.1: 91 percent / CaCO3; methyl iodide / acetonitrile; H2O / 24 h / 20 °C
8.1: 72 percent / Ni2B; NH2NH2*H2O / ethanol / 2 h / 80 °C
9.1: 96 percent / NaBH4 / methanol / 0 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; disodium hydrogenphosphate; nickel boride; tert.-butyl lithium; N-benzyl-trimethylammonium hydroxide; sodium hydrogencarbonate; hydrazine hydrate; triethylamine; 3-chloro-benzenecarboperoxoic acid; urea; calcium carbonate; sodium iodide; methyl iodide;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo047882v