Multi-step reaction with 9 steps
1: 1,4-dioxane / 18 h / 20 °C
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 18 h / 20 °C
3: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 2 h / -40 - -20 °C
4: chiral HPLC / Resolution of racemate
5: Nonafluorobutanesulfonyl fluoride; N-ethyl-N,N-diisopropylamine; triethylamine tris(hydrogen fluoride) / α,α,α-trifluorotoluene / 18 h / 20 °C
6: sodium periodate / osmium(VIII) oxide / water; methanol / 2 h / 20 °C
7: sodium tris(acetoxy)borohydride / dichloromethane / 0.5 h / 20 °C
8: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C
9: lithium hydroxide; methanol / 0.5 h / 20 °C
With
methanol; sodium periodate; copper(I) bromide dimethylsulfide complex; Nonafluorobutanesulfonyl fluoride; sodium tris(acetoxy)borohydride; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hydroxide;
osmium(VIII) oxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; α,α,α-trifluorotoluene; water;