Multi-step reaction with 10 steps
1.1: toluene / 0.17 h / 100 °C
1.2: 15 h / Reflux
2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C
3.1: diisobutylaluminium hydride / toluene / 2 h / -50 °C
4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / Cooling with ice
4.2: 3.5 h / 20 °C / Cooling with ice
5.1: magnesium / tetrahydrofuran
5.2: 2.3 h / 20 °C / Cooling with ice
6.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 6.3 h / Cooling with acetone-dry ice
7.1: zinc dibromide / dichloromethane / 68.5 h / 30 °C
8.1: CHIRALPAK? AD-H / hexane; isopropyl alcohol
9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 1-methyl-pyrrolidin-2-one / 3.08 h / 20 °C
10.1: sodium tetrahydroborate; ethanol / tetrahydrofuran / 0.83 h / Cooling with ice
With
sodium tetrahydroborate; ethanol; sodium hydride; diisobutylaluminium hydride; magnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc dibromide; (bis-(2-methoxyethyl)amino)sulfur trufluoride;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; mineral oil;