Multi-step reaction with 12 steps
1.1: N-Bromosuccinimide; water / tetrahydrofuran / 0.5 h / 20 °C
2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h
2.2: 20 °C
3.1: ammonium hydroxide; trimethylphosphane / water; pyridine / 2 h / 20 °C
4.1: sodium hydrogencarbonate / 1,4-dioxane / 2 h / 20 °C
5.1: triethylamine / dichloromethane / 5 h / 0 °C
6.1: pyridine / 0.17 h / 110 °C / Microwave irradiation
7.1: triethylamine / dichloromethane / 0.67 h
8.1: lithium hydroxide / tetrahydrofuran / 20 h / 20 °C
9.1: pyridine / 5.08 h / 20 °C
10.1: palladium on activated charcoal; hydrogen / isopropyl alcohol / 16 h
11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 3 h / 100 °C
12.1: AD-H chiral column / ethanol; n-heptane / Resolution of racemate
With
pyridine; ammonium hydroxide; N-Bromosuccinimide; palladium on activated charcoal; potassium tert-butylate; water; hydrogen; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hydroxide; trimethylphosphane;
In
tetrahydrofuran; 1,4-dioxane; pyridine; ethanol; n-heptane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;