Glyoxylic Acid → HCID 10704686, compound

Participants

Reaction Conditions

Reaction Steps

Glyoxylic acid (7.43 mL) was added dropwise to a solution of (R)—N-(1-phenylethyl)but-3-en-1-amine (7.80 g) in tetrahydrofuran (30 mL) at 60° C. over a period of 1.5 h. The reaction was heated at 60° C. for a further 7 h. Water (30 mL) and brine (30 mL) were added and the pH adjusted with 2M NaOH solution to pH 9. The aqueous was extracted with ethyl acetate (3×50 mL), the organics combined, washed with saturated aqueous NaHCO3 solution, water, brine, dried (MgSO4), filtered and evaporated to afford an orange oil (9.5 g). Purification (SiO2 chromatography using elution gradient 25% ethyl acetate in isohexane) afforded the subtitle product (3.10 g) as an orange oil.

Provenance & Evidence