Multi-step reaction with 8 steps
1.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 0.25 h / Cooling with ice
1.2: pH 7.5
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / Cooling with ice
2.2: 20 °C / Cooling with ice
3.1: magnesium / tetrahydrofuran / 20 °C / Cooling with ice
4.1: n-butyllithium / hexane; tetrahydrofuran / -70 - 20 °C
4.2: 3 h / 20 °C
5.1: hydrogen / platinum(IV) oxide / ethanol / 6 h / 20 °C / 760.05 Torr
6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 16 h / 20 °C
7.1: tributylphosphine; diamide / tetrahydrofuran / 16 h / 20 °C
8.1: trifluoroacetic acid / dichloromethane / 17 h / 20 °C
8.2: pH 4.4
With
n-butyllithium; tributylphosphine; diamide; water; hydrogen; sodium hydride; magnesium; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
platinum(IV) oxide;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil;