1: 97 percent / 10percent aq. NaOH / dioxane / 2 h 2: 1 h / 100 °C 3: n-BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature View Scheme

n-butyllithium in tetrahydrofuran; hexane 2 h; Ambient temperature; Yield given;

1: 4-(N,N-dimethylamino)benzoic acid; pyrrolidine / dichloromethane / |Reflux; |Inert atmosphere 2: sodium tetrahydroborate / methanol / 2 h / 0 °C View Scheme

1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 20 °C / |Inert atmosphere 1.2: 8 h / 20 °C 2.1: palladium on activated charcoal; hydrogen / ethanol / 5 h / 20 °C 3.1: diisobutylaluminium hydride / dichloromethane; hexane / 3 h / -78 °C 4.1: 4-(N,N-dimethylamino)benzoic acid; pyrrolidine / dichloromethane / |Reflux; |Inert atmosphere 5.1: sodium tetrahydroborate / methanol / 2 h / 0 °C View Scheme

1: palladium on activated charcoal; hydrogen / ethanol / 5 h / 20 °C 2: diisobutylaluminium hydride / dichloromethane; hexane / 3 h / -78 °C 3: 4-(N,N-dimethylamino)benzoic acid; pyrrolidine / dichloromethane / |Reflux; |Inert atmosphere 4: sodium tetrahydroborate / methanol / 2 h / 0 °C View Scheme

1: diisobutylaluminium hydride / dichloromethane; hexane / 3 h / -78 °C 2: 4-(N,N-dimethylamino)benzoic acid; pyrrolidine / dichloromethane / |Reflux; |Inert atmosphere 3: sodium tetrahydroborate / methanol / 2 h / 0 °C View Scheme

1: molecular sieves 4A, L-(+)-diethyl tartrate, titanium tetraisopropoxide, tert-butylhydroperoxide / CH2Cl2; 2,2,4-trimethyl-pentane / -20 °C 2: KOH / ethanol / 4 h / Ambient temperature 3: 99 percent / Et3N / CH2Cl2 / 1 h / 0 °C View Scheme