Multi-step reaction with 12 steps
1.1: 1H-imidazole / dichloromethane / 6 h / 0 - 20 °C
2.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C
3.1: pyridine-SO3 complex; triethylamine / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 20 °C
4.1: triethylamine / 12 h
4.2: 1 h / -78 °C
4.3: 1 h / -78 °C
5.1: sodium tetrahydroborate; water / tetrahydrofuran / 2 h / 20 °C
6.1: hydrogen / ethanol; water / 2 h / 2844.39 Torr
6.2: 16 h / 0 - 20 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 0 - 20 °C
8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
9.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C
10.1: trifluoroacetic acid / dichloromethane / 2.5 h / 0 °C
10.3: 16 h / 0 - 20 °C
11.1: trifluoroacetic acid / dichloromethane / 1.25 h / 0 °C
11.3: 16 h / 0 - 20 °C
12.1: trifluoroacetic acid / dichloromethane / 2.75 h / 0 °C
With
1H-imidazole; sodium tetrahydroborate; lithium borohydride; pyridine-SO3 complex; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil;