Multi-step reaction with 8 steps
1: 77 percent / p-TsOH / acetone; H2O / 24 h / Ambient temperature
2: 80 percent / imidazole / dimethylformamide / 0.67 h / 0 °C
3: 1.) (R,R)-bis(α-phenylethyl)ammonium chloride, n-BuLi / 1.) THF, hexane, -72 deg C, 10 min, then -100 deg C, 2 h; 2.) THF, hexane, -108 - -104 deg C, 35 min, then -70 deg C, 3 h
4: 88 percent / NaBH4 / ethanol / 7 h / -40 °C / 1.) -66 deg C
5: 98 percent / pyridine / tetrahydrofuran / 23 h / Ambient temperature
6: Pd(MeCN)2Cl2 / tetrahydrofuran / 17 h / Ambient temperature
7: 94 percent / K2CO3 / methanol / 4 h / Ambient temperature
8: 81 percent / dichlorodicyanobenzoquinone / dioxane / 22 h / Ambient temperature
With
pyridine; 1H-imidazole; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; n-butyllithium; (R,R)-(+)-bis[alpha-methylbenzyl]amine hydrochloride; potassium carbonate; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide; acetone;