Sodium Sulfate → HCID 10388777, compound

Participants

Reaction Conditions

Reaction Steps

Compound 2001 (16.1 g, 30 mmol) in dry tetrahydrofuran (THF, 150 ml) was added to a suspension of LiAlH4 (5.5 g, 145 mmol) in dry THF (200 ml). The suspension was stirred at 0° C. with a mechanical stirrer under argon overnight. The resultant gray slurry was quenched with EtOAc, followed by aqueous saturated Na2SO4 solution. During the addition of the Na2SO4 solution, a white precipitate formed and the solution became clear. Anhydrous Na2SO4 was added, the mixture was stirred for 15 minutes, and then filtered. The filter cake was washed well with ethyl acetate and the filtrate was concentrated in vacuo. The resulting solid was purified by flash chromatography (SiO2, hexanes:EtOAc 5:1) giving compound 2002 as a white solid (12.3 g 27.7 mmol, 92%). 1H NMR (500 MHz, CDCl3) δ 5.37-5.32 (m, 1H, C-6 H), 4.72 (brs, 1H, THP methine H), 3.95-3.88 (m, 1H, THP CH2O), 3.62-3.47 (m, 4H, THP CH2O & C-3 H & C-24 H), 1.01 (s, 3H, C-19 H), 0.93 (d, J=6.6 Hz, C-21 H), 0.68 (s, 3H, C-18 H); IR (CHCl3) 3610, 2900 cm-1 ; MS (CI/ isobutane) m/z 445 (M+1, 2%), 343 (M+1-THPOH, 100%); m.p. 130°-131° C.

Provenance & Evidence