Multi-step reaction with 10 steps
1.1: diethyl ether; acetonitrile; tetrahydrofuran / 0.5 h / 0 - 20 °C
1.2: 0.5 h / 0 - 20 °C
2.1: ethanol; sodium tetrahydroborate / 1.08 h / 5 - 20 °C
2.2: 20 - 40 °C
3.1: tetrahydrofuran / 20 °C
4.1: dichloromethane / 20 °C
5.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 0.5 h / 0 - 20 °C
5.2: 1 h / 0 - 20 °C
6.1: sodium t-butanolate / tris-(dibenzylideneacetone)dipalladium(0); (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / toluene / 1 h / 100 °C / Inert atmosphere
7.1: ammonium formate / palladium 10% on activated carbon / methanol / 1 h / 60 °C / Inert atmosphere
8.1: Chiralpak AD / isopropyl alcohol; n-heptane / 13501.4 Torr / Resolution of racemate
9.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 4-methyl-morpholine / N,N-dimethyl-formamide; tetrahydrofuran / 42 h / 50 - 60 °C
10.1: trifluoroacetic acid / acetonitrile; water / 5 h / 80 °C
10.2: 20 °C
With
4-methyl-morpholine; sodium tetrahydroborate; ethanol; ammonium formate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; sodium t-butanolate;
tris-(dibenzylideneacetone)dipalladium(0); palladium 10% on activated carbon; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl;
In
tetrahydrofuran; methanol; diethyl ether; n-heptane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile;