Aluminium lithium hydride → HCID 67418229, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 2h (150 mg, 0.33 mmol) in tetrahydrofuran (10 mL) at 5° C., LAH (76 mg, 2 mmol) was added. The resulting mixture was heated to reflux for 2 h and then cooled to 5° C., quenched with one drop of water. The precipitate formed was removed by filtration. The filtrate was diluted with 1N aqueous NaOH and extracted with EA. The organic layer was washed with brine and dried over anhydrous Na2SO4, concentrated in vacuo. The residue was purified by prep-HPLC to give compound 2 as a yellow solid (20 mg, 13% yield). 1H-NMR (400 MHz, CDCl3) δ 8.00 (dd, 1H, J=8.0, 2.0 Hz), 7.44 (m, 1H), 7.19-7.00 (m, 8H), 6.87-6.81 (m, 3H), 5.30 (d, J=17.6 Hz, 1H), 4.59-4.55 (m, 2H), 4.29 (m, 1H), 3.72 (s, 3H), 3.45 (d, J=12.4 Hz, 1H), 2.62 (dd, J=13.2, 10.4 Hz, 1H), 2.49-2.39 (m, 3H), 2.24 (s, 3H). MS (ESI+) m/z: 437 [M+H]+

Provenance & Evidence