Sodium borohydride → HCID 11194531, compound

A solution of ethyl 2-amino-2-phenylbutanoate (0.162 g, 0.782 mmol) in 1:3 v/v water/ethanol (4 mL) was reacted with sodium borohydride (0.151 g, 3.908 mmol) at reflux for four hours. The reaction was concentrated and partition between water (5 mL), ethyl ether (10 mL) and 1N aqueous sodium hydroxide (0.39 mL). Solid sodium chloride was added to saturate the aqueous and separate the phases. The aqueous phase was separated and re-extracted with ethyl ether (2×20 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 (0.116 g, 0.702 mmol, 90%). 1H NMR (300 MHz, DMSO-D6) δ ppm 0.59 (t, J=7.54 Hz, 3 H) 1.49-1.80 (m, 4 H) 3.44 (d, J=5.15 Hz, 2 H) 4.63 (t, J=5.52 Hz, 1 H) 6.89-7.76 (m, 5 H). MS (DCI) m/z 166 (M+H)+.

1. temperatureat reflux for four hours
2. concentrationThe reaction was concentrated
3. custompartition between water (5 mL), ethyl ether (10 mL) and 1N aqueous sodium hydroxide (0.39 mL)
4. additionSolid sodium chloride was added
5. concentrationto saturate the aqueous and
6. customseparate the phases
7. customThe aqueous phase was separated
8. extractionre-extracted with ethyl ether (2×20 mL)
9. washThe combined ethereal extracts were washed with brine (25 mL)
10. dry with materialdried over potassium carbonate
11. filtrationfiltered
12. concentrationconcentrated by rotary evaporation

ORD record

ord-e74eff4462ad4e1bab5743e5c5a0d87c

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07910595B2