Aluminium lithium hydride → HCID 86651331, compound

Participants

Reaction Steps

Lithium aluminium hydride (3 ml, 2M in THF, 6.0 mmol) was added dropwise to a solution of tert-butyl(2R,3S)-1,3-dihydroxy-4-(methylthio)butan-2-ylcarbamate (316 mg, 1.3 mmol) in tetrahydrofuran (5 ml) and the resulting suspension heated to reflux and left overnight. The reaction was cooled to ambient, quenched with water (0.25 ml), 15% aq NaOH (0.25 ml), and water (0.75 ml) and the resulting white suspension left to stir for 30 minutes. The suspension was then filtered through Celite®, washed with hot ethyl acetate, and the filtrate concentrated in vacuo to afford a mobile oil. The residue was purified by flash chromatography on silica gel eluting with 5% 7 N NH3 in MeOH/DCM to afford the title compound as an oil (120 mg, 57%). 1H NMR (CDCl3) δ 3.78 (m, 2H), 3.58 (dd, J=11.5, 3.9 Hz, 1H), 2.78 (dd, J=13.6, 4.3 Hz, 1H 1H), 2.64 (dd, J=13.6, 8.2 Hz, 1H), 2.50 (m, 1H), 2.47 (s, 3H), 2.15 (s, 3H). 13C NMR (CDCl3) δ 70.4, 64.5, 61.0, 39.7, 35.3, 16.6.

Provenance & Evidence