Multi-step reaction with 16 steps
1.1: sodium hydroxide; water / methanol / 0.5 h / 65 °C
1.2: pH ~ 2
2.1: polyphosphoric acid / 0.5 h / 75 - 100 °C
3.1: sodium carbonate / dichloromethane / 16 h / 0 - 20 °C
4.1: triethylamine / 1,3-bis-(diphenylphosphino)propane; palladium diacetate / N,N-dimethyl-formamide / 2 h / 80 °C
5.1: toluene / 72 h / 125 °C / Sealed vessel
5.2: 6 h / 20 °C
6.1: sodium hydrogencarbonate; sodium dithionite / Aliquot.(TM). 336 / water / 0.58 h / 100 °C
7.1: toluene-4-sulfonic acid / toluene / 1 h / Reflux
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.92 h / -65 - 0 °C
8.2: -60 °C
9.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C
10.1: sodium hydride / dimethyl sulfoxide; tetrahydrofuran; mineral oil / 0.5 h / 20 °C
10.2: 18.17 h / 20 °C
11.1: triethylamine / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 14 h / 90 °C
12.1: hydrogen / platinum(IV) oxide / ethyl acetate / 2 h
13.1: lithium hexamethyldisilazane / toluene; tetrahydrofuran / 0.25 h / 0 °C
14.1: hydrogenchloride; water / tetrahydrofuran / 16 h / 20 °C
15.1: tetrahydrofuran / 1 h / 5 - 10 °C
16.1: toluene-4-sulfonic acid; potassium hydrogensulfate / toluene / 4.5 h / 110 °C
With
hydrogenchloride; potassium hydrogensulfate; lithium aluminium tetrahydride; sodium dithionite; water; hydrogen; sodium hydride; sodium hydrogencarbonate; sodium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; sodium hydroxide; lithium hexamethyldisilazane;
platinum(IV) oxide; tris-(dibenzylideneacetone)dipalladium(0); 1,3-bis-(diphenylphosphino)propane; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil;