Methyl (hydroxymethoxy)acetate → HCID 12859191, compound

Participants

Reaction Steps

A benzene solution containing 541 mg (3.14 mmole) of (S)-2-(anilinomethyl)pyrrolidine and 425 mg (3.45 mmole) of methyl hydroxymethoxyacetate was heated under reflux for 30 minutes while removing formed water azeotropically, to form 3-methoxycarbonyl-2-phenyl-hexahydro-1H-pyrrolo[1,2-c]imidazole. After removing the solvent from the resulting reaction solution, the residue was dissolved in 20 ml of tetrahydrofuran, and 330 mg (3.48 mmole) of anhydrous magnesium chloride was added thereto, followed by heating under reflux for 1 hour. The reaction solution was cooled to -100° C., and a solution of 2-(2,5-dimethoxy-3,4,6-trimethylphenyl)ethylmagnesium bromide in tetrahydrofuran was added dropwise thereto. Completion of the reaction was examined by thin layer chromatography. Thereafter, a saturated aqueous ammonium chloride solution and ether were added, and the organic layer was separated, dried over sodium sulfate and freed from the solvent by evaporation. The residue was purified on alumina column to obtain 730 mg (55%) of 3-[3-(2,5-dimethoxy-3,4,6-trimethylphenyl)propanoyl]-2-phenyl-hexahydro-1H-pyrrolo[1,2-c]imidazole.

Provenance & Evidence