Multi-step reaction with 12 steps
1.1: sodium sulfate / diethyl ether / 5 h / 0 °C
2.1: n-butyllithium; borane-ammonia complex / tetrahydrofuran; hexane / 1 h / 0 - 40 °C
3.1: palladium(II) hydroxide; hydrogen / methanol / 18 h / 68 °C / 7500.75 Torr
4.1: triethylamine / dichloromethane / 15 h / 20 °C
5.1: 1H-imidazole / dichloromethane / 15 h / Reflux
6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 17 h / 20 °C
7.1: hydrogenchloride / water / 0.33 h / 20 °C
8.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C
9.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C
9.2: 3 h / 20 °C
10.1: hydrazine hydrate / ethanol / 2.5 h / Reflux
11.1: triethylamine / dichloromethane / 2.5 h / 20 °C
12.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 14 h / Reflux
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; n-butyllithium; borane-ammonia complex; potassium tert-butylate; hydrogen; palladium(II) hydroxide; sodium hydride; Dess-Martin periodane; hydrazine hydrate; sodium sulfate; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/jo5002627