TBAF tetrahydrofuran → 2-Bromo-1-[3-hydroxy-2-(tetrahydropyran-2-yloxy)propyl]-4-nitroimidazole

To tetrahydrofuran (120 ml) solution of 2-bromo-1-[3-(t-butyldimethylsilanyloxy)-2-(tetrahydropyran-2-yloxy)propyl)-4-nitroimidazole (12.7 g) prepared in Example 28, was added 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (30 ml) under stirring and ice-cooling condition, the reaction mixture was stirred at a room temperature overnight. The reaction mixture was concentrated under a reduced pressure and the residue was diluted with ethyl acetate, washed with water and an aqueous solution being saturated with sodium chloride. After being dried over anhydrous magnesium sulfate, the residue was concentrated under a reduced pressure, thus obtained residue was purified by use of a silica gel column chromatography (eluent: dichloromethane/ethyl acetate=10/1), there was obtained 2-bromo-1-[3-hydroxy-2-(tetrahydropyran-2-yloxy)propyl]-4-nitroimidazole (8.51 g, yield: 89%) as colorless liquid product.

1. temperatureice-cooling condition
2. stirringthe reaction mixture was stirred at a room temperature overnight
3. concentrationThe reaction mixture was concentrated under a reduced pressure
4. additionthe residue was diluted with ethyl acetate
5. washwashed with water
6. dry with materialAfter being dried over anhydrous magnesium sulfate
7. concentrationthe residue was concentrated under a reduced pressure, thus obtained residue
8. customwas purified by use of a silica gel column chromatography (eluent: dichloromethane/ethyl acetate=10/1)

ORD record

ord-99655074f19e49b9980fd121d3654b9d

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807843B2