Sodium borohydride → 1-(6-Bromopyridin-2-yl)ethane-1,2-diol

A solution of 1-(6-bromopyridin-2-yl)-2-hydroxyethanone (2.2 g, 10.18 mmol) in ethanol (127 mL) was charged with sodium borohydride (0.385 g, 10.18 mmol). After 30 minutes, the reaction was concentrated to dryness and then partitioned between ethyl acetate (50 mL) and 3:1 saturated aqueous sodium bicarbonate:water (25 mL). The layers were separated and the organic layer was washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated to afford the title compound. 1H NMR (600 MHz, DMSO): δ 7.69 (m, 1H), 7.46 (m, 2H), 5.50 (d, J=5.0 Hz, 1H), 4.69 (m, 1H), 4.49 (m, 1H), 3.61 (m, 1H), 3.46 (m, 1H).

1. concentrationthe reaction was concentrated to dryness
2. custompartitioned between ethyl acetate (50 mL) and 3:1 saturated aqueous sodium bicarbonate
3. customThe layers were separated
4. washthe organic layer was washed with brine (25 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-2bf238c9c0ec4e1da4fa1f40b9c79a50

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2