Multi-step reaction with 10 steps
1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C
2: ethyl acetate; water / 24 h / 20 °C
3: hydrogenchloride / 18.08 h / -78 - -10 °C
4: trifluoroacetic acid / dichloromethane / 20 °C
5: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 20 h / 100 °C / sealed tube; Inert atmosphere
6: hydrogen / palladium 10% on activated carbon / ethanol / 760.05 Torr
7: toluene-4-sulfonic acid; methanol / 1 h / 20 °C
8: water; lithium hydroxide / tetrahydrofuran / 2 h / 20 °C
9: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 22 h / 20 °C
10: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C
With
hydrogenchloride; methanol; water; hydrogen; benzotriazol-1-ol; Dess-Martin periodane; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; pyridinium chlorochromate; trifluoroacetic acid; lithium hydroxide;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium 10% on activated carbon;
In
tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;