Multi-step reaction with 8 steps
1.1: sulfuric acid / water / 0.75 h / 90 °C
2.1: acetic acid; sodium nitrite / water / 0.5 h / 0 °C
3.1: 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
3.2: 0.25 h / 20 °C
4.1: di-isopropyl azodicarboxylate; trimethylphosphane / toluene / 0.5 h / -50 °C
5.1: methanol; sodium hydroxide; water / 20 h / Heating / reflux
5.2: 2 h / Heating / reflux
6.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 23 °C
7.1: sodium azide / water; acetone / 0.5 h / 0 °C
7.2: 0.67 h / Heating / reflux
8.1: sodium carbonate / water; toluene / 2 h / 23 °C
With
methanol; sodium hydroxide; borane N,N-diethylaniline complex; sodium azide; oxalyl dichloride; di-isopropyl azodicarboxylate; sulfuric acid; water; sodium carbonate; acetic acid; N,N-dimethyl-formamide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; sodium nitrite; trimethylphosphane;
In
dichloromethane; water; acetone; toluene;