Ammonia → HCID 59134341, compound

Participants

Reaction Steps

Under nitrogen stream, sodium (90 mg, 3.91 mmol) was added to liquid ammonia (5 mL) at −78° C., and the resulting mixture was stirred. A solution of 1-benzyl-7-hydroxy-6,6-dimethyl-8-phenetylamino-3,6,7,8-tetrahydro-1H-pyrano[2,3-f]indole-2-one (173 mg, 0.39 mmol) in THF (2 mL) was added dropwise at −45° C., and the resulting mixture was stirred for 15 minutes. Upon the completion of the reaction, saturated ammonium chloride aqueous solution was added thereto, the resulting solution was extracted with ethyl acetate. The resulting organic phase was washed with water and then with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, concentrated and purified by silica gel column (ethyl acetate) to obtain the aimed product (yield: 19%).

Provenance & Evidence