Multi-step reaction with 8 steps
1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 11 h / Heating
1.2: 0.5 h / 0 °C
1.3: 11 h / 0 - 20 °C
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C
3.1: hydrogenchloride / water; dichloromethane; methanol / 18 h / 20 °C
4.1: 1H-tetrazole / dichloromethane / 24 h / 20 °C / Molecular sieve
4.2: 1 h / 0 °C / Molecular sieve
5.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 60 °C
6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C
6.2: 4 h / 0 - 20 °C
7.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 40 °C
8.1: N,O-Bis(trimethylsilyl)trifluoroacetamide; trimethylsilyl bromide / dichloromethane; toluene / 1 h
8.2: 1 h / 0 - 20 °C
8.3: Dowex-1X8 (HCO3-) resin
With
1H-imidazole; 1H-tetrazole; hydrogenchloride; trimethylsilyl bromide; tetrabutyl ammonium fluoride; N,O-Bis(trimethylsilyl)trifluoroacetamide; sodium hydride; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1039/c6ob01062h