Hydrochloric Acid → HCID 11439682, compound

Participants

Reaction Steps

To a solution of 1-allyl 3-tert-butyl (2S)-2-[(methoxymethoxy)methyl]-2,5-dihydro-1H-pyrrole-1,3-dicarboxylate (296 mg, 0.90 mmol) in methanol (2 ml) was added hydrochloric acid/methanol(5 ml) and the mixture was stirred overnight. To the solution was added toluene and the solvent was removed in vacuo. To the residue were added methanol and toluene and the solvent was again removed in vacuo. The residue was dissolved in THF (8 ml) and thereto were added at 0–5° C. 2,6-lutidine (0.84 ml, 7.2 mmol) and tert-butyldimethylsilyltriflate (0.83 ml, 3.6 mmol). The mixture was stirred at room temperature for 1 hour and thereto was added at 0–5° C. a solution of trimethylsilyldiazomethane in hexane (2M, 0.45 ml, 0.90 mmol). Thirty minutes later the mixture was raised to room temperature and stirred for 30 minutes. Thirty minutes later to the mixture were added 1N hydrochloric acid and a saturated aqueous sodium chloride solution, and the mixture was separated with a separating funnel. The organic layer was dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was purified with silica gel (26 g) chromatography (hexane/ethyl acetate=1/5) to give 1-allyl 3-methyl (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,5-dihydro-1H-pyrrole-1,3-dicarboxylate (71 mg, 22%).

Provenance & Evidence