Sodium borohydride → HCID 54776080, compound

The product of Example 437A (0.497 g, 2.494 mmol) in 1:3 v/v water/ethanol (12 mL) was reacted with sodium borohydride (0.481 g, 12.47 mmol) at reflux for 4 hours. The reaction was concentrated by rotary evaporation partition between water (5 mL), ethyl ether (25 mL), 1N aqueous sodium hydroxide (1.25 mL). Solid sodium chloride was added to saturate separate phases. The aqueous was re-extracted with ethyl ether (25 mL). The combined ethereal extracts were washed with brine (25 mL), dried over potassium carbonate, filtered, and concentrated by rotary evaporation to afford the title compound as an oil (0.330 g, 2.099 mmol, 84%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.35 (s, 3 H) 1.96 (s, 2 H) 3.33-3.42 (m, 2 H) 4.91 (t, J=5.70 Hz, 1 H) 6.89-6.95 (m, 2 H) 7.28 (dd, J=3.49, 2.76 Hz, 1 H). MS (DCI) m/z 158 (M+H)+.

1. temperatureat reflux for 4 hours
2. concentrationThe reaction was concentrated by rotary evaporation
3. custompartition between water (5 mL), ethyl ether (25 mL), 1N aqueous sodium hydroxide (1.25 mL)
4. additionSolid sodium chloride was added
5. concentrationto saturate
6. customseparate phases
7. extractionThe aqueous was re-extracted with ethyl ether (25 mL)
8. washThe combined ethereal extracts were washed with brine (25 mL)
9. dry with materialdried over potassium carbonate
10. filtrationfiltered
11. concentrationconcentrated by rotary evaporation

ORD record

ord-03c014788e784f878119d62eb63aeafb

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07910595B2