(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile → HCID 178431172, compound

Participants

Reaction Steps

1.89 g of ethyl N-cyanobenzimidate was dissolved in 5 ml of dimethylformamide, and 2.15 g of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-amino-2H-benzo[b]pyran-3-ol was added thereto. The mixture was reacted at a temperature of from 100° to 120° C. for 2 hours. The reaction mixture was cooled, then dissolved in 100 ml of ethyl acetate, washed four times with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The residual oily substance was purified by silica gel column chromatography to obtain 1.32 g of the above identified compound in the form of crystals.

Provenance & Evidence