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0 °C

To a solution of tert.-butyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-hydroxybutanoate (5.49 g, 20.0 mmol) in toluene (40.0 ml), sodium methoxide (1M in methanol) (30 ml) was added at 0° C. in an argon atmosphere and stirred at 0° C. for 30 minutes. After dropwise adding 1N hydrochloric acid (30.5 ml) at 0° C. over 10 minutes, the mixture was stirred at 0° C. for 10 minutes. After evaporating off the most of the organic solvent under reduced pressure, the residual mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline and a phosphate buffer (pH 7.0). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:acetone=2:1) to give pure 1-methyl 6-tert.-butyl 2,4-dihydroxyadipate (3.69 g, 14.9 mmol). Yield, 74.3 %.

1. stirringthe mixture was stirred at 0° C. for 10 minutes
2. customAfter evaporating off the most of the organic solvent under reduced pressure
3. extractionthe residual mixture was extracted with ethyl acetate
4. washThe organic layer was washed with a saturated saline
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure