Multi-step reaction with 8 steps
1.1: borane N,N-diethylaniline complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 3 h / 30 °C
1.2: 0.25 h / 20 °C
2.1: di-isopropyl azodicarboxylate; trimethylphosphane / toluene / 0.5 h / -50 °C
3.1: methanol; sodium hydroxide; water / 20 h / Heating / reflux
3.2: 2 h / Heating / reflux
4.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 23 °C
5.1: sodium azide / water; acetone / 0.5 h / 0 °C
5.2: 0.67 h / Heating / reflux
6.1: sodium carbonate / water; toluene / 2 h / 23 °C
7.1: N-ethyl-N,N-diisopropylamine / tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 1 h / 50 °C
8.1: N-chloro-succinimide; acetic acid / water / 2 h / 23 °C
With
methanol; sodium hydroxide; N-chloro-succinimide; borane N,N-diethylaniline complex; sodium azide; oxalyl dichloride; di-isopropyl azodicarboxylate; water; sodium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; trimethylphosphane;
tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
1,4-dioxane; dichloromethane; water; acetone; toluene;