Sodium borohydride → HCID 54776080, compound

Participants

Reaction Steps

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)+.

Provenance & Evidence