Ethyl Acetate → HCID 54374690, compound

Participants

Reaction Steps

To a solution of 5.7 g (19.43 mmol) of (2S,5R)-1-benzyloxycarbonyl-5-hydroxy-2-methoxycarbonylpiperidine, which was prepared by the procedure described in P.D. Bailey et al., Tetrahedron Letters. 29, 2231 (1988), in 250 ml of methanol was added 570 mg of 5% palladium-carbon, and the mixture was hydrogenated at atmospheric pressure and room temperature for 1 hours. The catalyst was removed by filtration, and the solvent was removed. To a solution of this residue in 30 ml of dioxane was dropwise added a solution of 6.85 g (21.45 mmol) of p-nitrobenzyloxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine in 50 ml of dioxane, and the mixture was stirred for 1.5 hours at room temperature. To the reaction mixture was added 300 ml of ethyl acetate, the organic layer was washed successively with 50 ml of 1N HCl(×2), 50 ml of water and saturated aqueous sodium chloride. After the extract was dried over anhydrous sodium sulfate, the solvent was removed. The residue was purified by silica gel column chromatography (Wakogel® C-300, elution with ethyl acetate - hexane system) to give 5.81 g (yield: 88%) of the title compound.

Provenance & Evidence