Multi-step reaction with 14 steps
1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1.5 h / 0 - 25 °C / Inert atmosphere
2: boron trifluoride diethyl etherate / acetone / 15 h / 25 °C / Inert atmosphere
3: diethyl ether / 2 h / -78 °C / Inert atmosphere
4: zinc tetrahydridoborate*Et2O; cerium(III) chloride heptahydrate / methanol / 2.5 h / 0 - 25 °C / Inert atmosphere
5: water; acetic acid / 15 h / 50 °C
6: pyridine / 1 h / 0 °C / Inert atmosphere
7: pyridine / 0.67 h / 0 - 25 °C / Inert atmosphere
8: acetonitrile / 1.5 h / 0 - 25 °C / Inert atmosphere
9: sodium chloride / ethyl acetate; water; acetonitrile / 0.5 h / 25 °C
10: sodium tetrahydroborate; oxygen / N,N-dimethyl-formamide / 3 h / 25 °C
11: 1H-tetrazole / dichloromethane / 2 h / 0 - 25 °C / Inert atmosphere
12: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.33 h / Inert atmosphere
13: sodium methylate; methanol / dichloromethane / 0.5 h / 25 °C / Inert atmosphere
14: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere
With
4-methyl-morpholine; pyridine; 1H-tetrazole; methanol; sodium tetrahydroborate; zinc tetrahydridoborate*Et2O; cerium(III) chloride heptahydrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; oxygen; sodium methylate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; sodium chloride;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1039/c3md00033h