2H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo- → (3aR*,10aS*)-9-(4-Benzyloxybenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Participants

Reaction Steps

To a solution of (3aR*,10aS*)-9-(4-benzyloxybenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b ]cyclopenta[e][1,4]diazepin-10(1H)-one (3.1 g, 7.8 mmol) in 1,2-dichloroethane was added phthalimidoacetyl chloride (1.9 g, 8.5 mmol). The mixture was refluxed for 17 hours. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate. The aqueous layer was separated. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, dried over magnesium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure. The concentrate was parified by silica-gel column chromatography (hexane-ethyl acetate 1:3), which was crystallized from diethyl ether to give the desired product (1.9 g, 42%), m.p.179°-181° C.

Provenance & Evidence