Trimethyl orthoformate → HCID 67103541, compound

Participants

Reaction Steps

The compound (1.78 g) obtained in Example 64-1 was dissolved in methanol (30 ml) and added with trimethyl orthoformate (1.8 ml), acetic acid (1.0 ml), and sodium cyanoborohydride (0.324 g). The mixture was gradually added with a methanol solution (5.0 ml) containing 1-methyl-2-imidazole carboxaldehyde (0.550 g) and the whole was stirred at room temperature for 1 hour. Further, sodium cyanoborohydride (0.486 g) and a methanol solution (6.0 ml) containing 1-methyl-2-imidazole carboxaldehyde (0.660 g) were added thereto and the whole was stirred at room temperature for 63 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and washed with a saturated aqueous sodium hydrogen carbonate solution and then the whole was subjected to extraction with chloroform. The organic layer was a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (1.18 g) as a colorless oily substance.

Provenance & Evidence