Multi-step reaction with 12 steps
1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -20 °C
2.1: sodium methylate / methanol / 0.5 h / 20 °C / pH 10
2.2: Dowex H+
3.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide; acetonitrile / 1 h / 20 °C
4.1: N-iodo-succinimide / dichloromethane / 0.33 h / 20 °C / Inert atmosphere; Molecular sieve
4.2: 1 h / -30 °C / Inert atmosphere; Molecular sieve
5.1: water; acetic acid / dichloromethane / 48 h / 20 °C
6.1: N-iodo-succinimide / dichloromethane / 0.33 h / 20 °C / Inert atmosphere; Molecular sieve
6.2: 1 h / -30 °C / Inert atmosphere; Molecular sieve
7.1: sodium methylate / methanol / 0.33 h / 20 °C
7.2: Dowex H+
8.1: hydrazine / ethanol / 70 °C
9.1: dmap / pyridine / 2 h / 20 °C
10.1: pyridine / 20 °C
11.1: sodium methylate / methanol / 0.5 h
11.2: 1 h
11.3: Dowex H+
12.1: 10% palladium on activated charcoal; hydrogen / water / 1 h
With
dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 10% palladium on activated charcoal; water; hydrogen; sodium methylate; toluene-4-sulfonic acid; acetic acid; hydrazine;
In
pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.carres.2011.03.036