Multi-step reaction with 10 steps
1: toluene-4-sulfonic acid / toluene / 3 h / Reflux
2: toluene-4-sulfonic acid; orthoformic acid triethyl ester / 1,4-dioxane; N,N-dimethyl-formamide / 3 h / 20 °C / 97.51 - 120.01 Torr
3: sodium hydride / 1,4-dioxane / 65 °C
4: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 8 h / 0 - 20 °C
5: acetic acid / water / 2 h / 60 °C
6: pyridine / 3 h / 20 °C
7: palladium 10% on activated carbon; hydrogen / methanol / 5 h / 760.05 Torr
8: 1H-tetrazole / acetonitrile / 8 h / 20 °C
9: dihydrogen peroxide / water; acetonitrile / 0.58 h / -78 - 20 °C
10: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / 0 - 20 °C
With
1H-tetrazole; dmap; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; orthoformic acid triethyl ester;
In
1,4-dioxane; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/ja302099u