Multi-step reaction with 14 steps
1.1: hydrogenchloride / water / 4 h / 80 °C
2.1: diphenyl phosphoryl azide; triethylamine / toluene / 1 h / 70 °C
3.1: triethylamine / toluene / 5 h / 80 °C
4.1: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 5 h / 20 °C
5.1: borane-THF / tetrahydrofuran / 4 h / -5 °C
6.1: Chiral Pak AD-H 250 column / ethanol; carbon dioxide / 40 °C / Resolution of racemate
7.1: palladium 10% on activated carbon; hydrogen / methanol / 16 h / 2585.81 Torr
8.1: acetic acid / toluene / 2 h / Reflux
9.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 2 h / Molecular sieve
10.1: diethyl ether / 0.5 h / 0 °C
11.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 2 h / Molecular sieve
12.1: diethyl ether / 0.5 h / 0 °C
13.1: hydroxylamine hydrochloride; triethylamine / water; isopropyl alcohol / 6 h / Reflux
13.2: 16 h / 0 °C
14.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C
With
hydrogenchloride; tetrapropylammonium perruthennate; borane-THF; lithium hydroxide monohydrate; diphenyl phosphoryl azide; palladium 10% on activated carbon; hydroxylamine hydrochloride; water; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; 4-methylmorpholine N-oxide; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; carbon dioxide; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
3.1: Curtius rearrangement / 10.1: Grignard reaction / 12.1: Grignard reaction;
DOI:10.1055/s-0031-1289884