Aluminium lithium hydride → HCID 86651331, compound

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.

1. temperaturethe resulting suspension heated
2. temperatureto reflux
3. temperatureThe reaction was cooled to ambient,
4. customquenched with water (0.25 ml), 15% aq NaOH (0.25 ml), and water (0.75 ml)
5. waitthe resulting white suspension left
6. filtrationThe suspension was then filtered through Celite®
7. washwashed with hot ethyl acetate
8. concentrationthe filtrate concentrated in vacuo
9. customto afford a mobile oil
10. customThe residue was purified by flash chromatography on silica gel eluting with 5% 7 N NH3 in MeOH/DCM

ORD record

ord-a75def9dbaa44e1abf8d8a0782cb1d5f

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08383636B2