Multi-step reaction with 13 steps
1.1: sodium hydroxide / methanol / 2 h / 20 °C / Inert atmosphere
2.1: pyridinium chlorochromate / dichloromethane / 4 h / Molecular sieve; Inert atmosphere
3.1: sodium hexamethyldisilazane / 0.17 h / 0 °C / Inert atmosphere
3.2: 1 h / Inert atmosphere
4.1: chloroamine-T / dichloromethane; water; ethanol / 12 h / 50 °C
5.1: boric acid; hydrogen / water; ethanol / 22 h / 760.05 Torr / Inert atmosphere
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 20 h / 65 °C / Inert atmosphere
7.1: sodium acetate; acetic acid / 12 h / 80 °C / Inert atmosphere
8.1: hydrogenchloride; water / methanol; tetrahydrofuran / 16 h / 50 °C
9.1: toluene-4-sulfonic acid / acetone / 0.33 h / Inert atmosphere
9.2: 0.33 h
10.1: triethylamine; dmap / dichloromethane / 2 h / 0 °C / Inert atmosphere
11.1: hydrogenchloride; water / methanol; tetrahydrofuran / 16 h / 50 °C
12.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C / Inert atmosphere
12.2: 1 h / 0 °C / Inert atmosphere
13.1: ammonium cerium (IV) nitrate / water; ethyl acetate; acetonitrile / 1.25 h / 0 °C
With
hydrogenchloride; dmap; ammonium cerium (IV) nitrate; water; hydrogen; sodium acetate; chloroamine-T; boric acid; sodium hexamethyldisilazane; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; sodium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; acetonitrile;
DOI:10.1002/chem.201402254