L-Valine → HCID 14387464, compound

Participants

Reaction Steps

A mixture of L-valine (29.29 g, 250 mmol), and cyclohexanone (51.8 mL, 500 mmol, Aldrich Inc, Milwaukee, Wis.) was agitated in an atmosphere of hydrogen (pressure, 23.4-51.1 psi) at room temperature in 370 mL ethanol in the presence of Pd/C (20%, 3 g) until the absorption of hydrogen had ceased. The mixture was filtered, and this ethanolic filtrate was set aside, then the filter cake washed with 450 mL 1 M HCl. The ethanolic filtrate was concentrated to dryness and the residue dissolved in the aqueous filtrate above, which was treated with concentrated aqueous sodium hydroxide (29.8%) to adjust the pH to 5.5. The white solid precipitated out which was isolated via filtration, washed with two 150 mL portions of ethanol and dried under vacuum to give 37.4 g (70%) of the pure titled compound as a white solid; mp >300° C. APCI-MS m/z 200.2 (MH+).

Provenance & Evidence