反应详情

A solution of (2S,3R)-3-(4-benzyloxy-2-methoxy-phenyl)-2-ethoxy-3-hydroxy-propionic acid methyl ester (100 mg, 200 μmol) and oxalic acid dihydrate (150 mg, 1.2 mmol) in isopropanol (2 ml) was hydrogenated at a pressure of 50 atmospheres over 10% palladium on charcoal (20 mg) at ambient temperature for 6.5 h. The catalyst was filtered off and the solvent evaporated under reduced pressure. The residue was dissolved in ice water/aqueous sodium bicarbonate solution 1/1 and extracted two times with ethyl acetate. The combined extracts were washed two times with ice water/brine 1/1 and dried over sodium sulfate. The solvent was removed under reduced pressure to give a yellow liquid which was purified by column chromatography (silica gel, cyclohexane/AcOEt) to yield 43 mg (170 μmol, 85%) of the title compound as light yellow liquid.

1. filtrationThe catalyst was filtered off
2. customthe solvent evaporated under reduced pressure
3. dissolutionThe residue was dissolved in ice water/aqueous sodium bicarbonate solution 1/1
4. extractionextracted two times with ethyl acetate
5. washThe combined extracts were washed two times with ice water/brine 1/1
6. dry with materialdried over sodium sulfate
7. customThe solvent was removed under reduced pressure
8. customto give a yellow liquid which
9. customwas purified by column chromatography (silica gel, cyclohexane/AcOEt)