Multi-step reaction with 11 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / α,α,α-trifluorotoluene / 1 h / 70 °C / Irradiation
2.1: N,N-dimethyl-formamide / 70 °C
3.1: chloro-trimethyl-silane / 2.25 h / 79 °C
4.1: triethylamine / hexanes; acetonitrile / 3 h / 20 °C
5.1: N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate / cyclohexane / 5 h / 86 °C
6.1: N,N,N',N'-tetramethylguanidine / N,N-dimethyl-formamide / 2 h / 50 - 80 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / -70 - 10 °C
7.2: 0.5 h
8.1: N-ethyl-N,N-diisopropylamine; Methanesulfonic anhydride / chloroform / 3.5 h / 20 - 65 °C
9.1: hydrogenchloride / water / 0 - 20 °C
10.1: isopropylamine / methanol; acetonitrile / Resolution of racemate
11.1: sodium sulfate / methanol; dichloromethane / 16.5 h
11.2: 23.5 h
With
hydrogenchloride; N-Bromosuccinimide; lithium aluminium tetrahydride; chloro-trimethyl-silane; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; sodium sulfate; isopropylamine; triethylamine; N-ethyl-N,N-diisopropylamine; N,N,N',N'-tetramethylguanidine; Methanesulfonic anhydride; dibenzoyl peroxide;
In
tetrahydrofuran; methanol; hexanes; dichloromethane; chloroform; cyclohexane; α,α,α-trifluorotoluene; water; N,N-dimethyl-formamide; acetonitrile;