Multi-step reaction with 11 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 20 °C
2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 1 h / 0 °C
2.2: 3 h / 20 °C
3.1: aluminum (III) chloride; sodium iodide / dichloromethane; acetonitrile / 1 h / 0 °C
4.1: (R)-(-)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanoltrimethylsilyl ether; benzoic acid / toluene / 88 h / 20 °C
5.1: triethylamine / tetrahydrofuran / 0 - 20 °C
6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 96 h / 20 °C
7.1: tetrahydrofuran / 4 h / Reflux
8.1: 5% Pd-BaSO4; hydrogen / ethyl acetate / 0.67 h / 20 °C / 750.08 Torr
9.1: toluene-4-sulfonic acid / tetrahydrofuran / 72 h / 20 °C
10.1: pyridinium chlorochromate / dichloromethane / 5 h / 20 °C
11.1: iodine; magnesium / diethyl ether; benzene / 16 h / Reflux
With
1H-imidazole; aluminum (III) chloride; osmium(VIII) oxide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; (R)-(-)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanoltrimethylsilyl ether; 5% Pd-BaSO4; hydrogen; iodine; toluene-4-sulfonic acid; magnesium; 4-methylmorpholine N-oxide; triethylamine; benzoic acid; pyridinium chlorochromate; sodium iodide;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
DOI:10.1002/chem.201102192