Ethanol → HCID 59226561, compound

Participants

Reaction Steps

To a solution of (R)-4-benzyl-3-((2R,3R)-3-(tert-butyldimethylsilyloxy)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropanoyl)oxazolidin-2-one (1.0 equiv.) and ethanol (3.0 equiv.) in THF (0.09 M) was added LiBH4 (1.0 equiv.) at −40° C. The reaction mixture was allowed to warm up to rt slowly and stirred at that temperature for 12 hours. The solution was cooled back to −40° C. and additional LiBH4 (0.3 equiv.) was added. After warming back up to rt and stirring for 2 hours the solution was then diluted with diethyl ether and 1N NaOH) was added. The resulting mixture was extracted with ethyl acetate, the organic layer was separated, washed with NaCl(sat.), dried over magnesium sulfate, filtered, and concentrated. The residue was purified via silica gel column chromatography (10-30% EtOAc/n-heptanes) yielding (2S,3R)-3-(tert-butyldimethylsilyloxy)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropan-1-ol in (75%). LC/MS=247.1 (M+H-ketal-H2O), Rt=0.64 min.

Provenance & Evidence