Multi-step reaction with 8 steps
1.1: zinc / tetrahydrofuran / 60 - 65 °C
2.1: tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Large scale
3.1: potassium osmate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; 4-methylmorpholine N-oxide / acetone; water / 8.5 h / 10 - 25 °C / Large scale
4.1: sodium periodate / acetone; water / 33 h / 10 - 30 °C / Inert atmosphere; Large scale
5.1: sodium hexamethyldisilazane; tris(pyrrolidino)phosphine oxide / tetrahydrofuran / 1.4 h / 0 - 10 °C / Inert atmosphere; Large scale
5.2: 1 h / -38 - -32 °C / Inert atmosphere; Large scale
6.1: potassium carbonate / acetone / 4 h / Reflux; Large scale
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 35 - 40 °C / Large scale
8.1: zinc(II) chloride; hydroquinone / water; 1,4-dioxane / 6 h / Inert atmosphere; Reflux; Large scale
8.2: 15 h / 20 °C / Inert atmosphere; Large scale
With
potassium osmate; sodium periodate; tris(pyrrolidino)phosphine oxide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; potassium carbonate; 4-methylmorpholine N-oxide; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; hydroquinone; zinc(II) chloride; zinc;
In
tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; acetone;
5.2: |Wittig Olefination;
DOI:10.1021/op300188x