Water → 2-(6-Bromopyridin-2-yl)propane-1,2-diol

To a solution of 2-bromo-6-isopropenylpyridine (0.510 g, 2.57 mmol) in acetone (1 mL) and water (2 mL) was added N-methylmorpholine N-oxide (0.317 g, 2.70 mmol) followed by osmium tetroxide (0.257 mL, 0.013 mmol). After 16 hours, dithionite (0.05 g) and water (1.5 mL) were added. After an additional 15 minutes, the reaction mixture was filtered though a pad of Celite. The filter was rinsed with acetone (3×1.5 mL), and the filtrate was concentrated under vacuo to remove the acetone. The remaining liquid was diluted with 9:1 chloroform:isopropanol (4 mL) and aqueous hydrogen chloride (2 M) was added until the aqueous layer was acidic. The layers were separated, and the acidic (pH=1) aqueous layer was extracted with 9:1 chloroform:isopropanol (2×4 mL). The combined organic layers were washed with 3:1 water:brine (2.5 mL), saturated aqueous sodium bicarbonate (4 mL), and brine (4 mL), dried over sodium sulfate, filtered, and concentrated to afford the title compound.

1. waitAfter an additional 15 minutes
2. filtrationthe reaction mixture was filtered though a pad of Celite
3. washThe filter was rinsed with acetone (3×1.5 mL)
4. concentrationthe filtrate was concentrated under vacuo
5. customto remove the acetone
6. additionThe remaining liquid was diluted with 9:1 chloroform
7. additionisopropanol (4 mL) and aqueous hydrogen chloride (2 M) was added until the aqueous layer
8. customThe layers were separated
9. extractionthe acidic (pH=1) aqueous layer was extracted with 9:1 chloroform
10. washThe combined organic layers were washed with 3:1 water
11. dry with materialbrine (2.5 mL), saturated aqueous sodium bicarbonate (4 mL), and brine (4 mL), dried over sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated

ORD-Eintrag

ord-be45f336f80b4993882b4fb5d942a17b

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08367706B2