Arachidonyl azide → Arachidonyl amine

Participants

Reaction Steps

The crude azide was reduced to the title amine as follows: To a magnetically stirred solution of 132 mg (0.43 mmol) of arachidonyl azide in 3 mL of dry diethyl ether was added 4 mL of 1.0 M solution of lithium aluminum hydride (4.0 mmol) in THF dropwise at room temperature. The reaction mixture was refluxed for 3 hours and then quenched with wet diethyl ether. The white suspension was filtered, and the filtrate was evaporated to dryness. Chromatography on silica gel (10–50% MeOH in dichloromethane) gave 65 mg (51%) of arachidonylamine as a white solid: TLC (20% EtOAc—CH2Cl2) Rf 0.33; 1H NMR (200 MHZ, CDCl3) δ5.38 (m, 8H), 2.82 (m, 6H), 2.70 (t, J=6.6 Hz, 2H), 2.08 (m, 4H), 1.40 (m, 4H), 1.26 (m, 6H), 0.89 (t, J=6.4 Hz, 3H). Anal. (C20H35N)C, H, N.

Provenance & Evidence