Ammonia → HCID 67151589, compound

Participants

Reaction Steps

To a solution of (E)-(S)-2-amino-4-(4-nitro-phenyl)-but-3-en-1-ol (2.5 g) in methanol (90 ml) at room temperature was added sodium acetate (3.0 g) followed by a solution of cyanogen bromide (1.65 g) in methanol (10 ml) dropwise over 15 minutes. The reaction mixture was stirred for 2 days, then 25% aqueous ammonia (8.2 ml) was added and the solution stirred for 1 hour at room temperature. The solvent was evaporated in vacuo and the residue purified by Isco chromatography (column: Silicycle Si-Amine, AcOEt) to give (S)-4-[(E)-2-(4-nitro-phenyl)-vinyl]-4,5-dihydro-oxazol-2-ylamine (950 mg) as a yellow oil. MS (ISP): 234.1 ([M+H]+).

Provenance & Evidence