Sodium Fluoride → Arachidonyl amine

To a magnetically stirred solution of 132 mg (0.43 mmol) of arachidonyl azide in 3 mL of Et2O, 4 mL of a 1.0 M LAH solution in THF (4.0 mmol) was added dropwise at room temperature. The reaction mixture was refluxed for 3 h and then it was cooled to ambient temperature. 210 mg (5 mmol) of NaF was added and the reaction was quenched with wet Et2O. The white mixture was filtered and the solvent was evaporated to dryness. Silica gel chromatography (eluents: CH2Cl2/MeOP-up to 50% MeOH), evaporation of solvent, followed by Millipore filtration of a CH2Cl2 solution of the product then gave 78.9 mg (0.28 mmol, 64% yield) of arachidonyl-amine as a colorless oil. TLC (EtOAc/CH2Cl2 (20:80)) Rf 0.33; 1H NMR (200 MHz, CDCl3) δ 5.38 (m, 8 H), 2.82 (m, 6 H), 2.70 (t, 2 H, J=6.6 Hz), 2.08 (m, 4 H), 1.40 (m, 4 H), 1.26 (m, 6 H), 0.89 (t, 3 H, J=6.4 Hz).

1. temperatureThe reaction mixture was refluxed for 3 h
2. customthe reaction was quenched with wet Et2O
3. filtrationThe white mixture was filtered
4. customthe solvent was evaporated to dryness
5. customSilica gel chromatography (eluents: CH2Cl2/MeOP-up to 50% MeOH), evaporation of solvent
6. filtrationfollowed by Millipore filtration of a CH2Cl2 solution of the product

ORD record

ord-edebc31a72204380924c943f110eb1b0

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07589220B2