Water → (3aS)-1,2,3,3a,4,5-Hexahydropyrrolo[1,2-a]quinoxaline

Participants

Reaction Steps

A solution of 1.04 g of (3aS)-1,2,3,3a,4,5-hexahydro-pyrrolo[1,2-a]quinoxalin-4-one prepared in Reference Example 9 in 30 ml of anhydrous tetrahydrofuran was dropwise added, with ice-cooling, to a suspension of 0.53 g of lithium aluminum hydride in 30 ml of anhydrous tetrahydrofuran over 30 minutes. After the dropwise addition, the mixture was refluxed with heating for 2 hours. The reaction solution was ice-cooled, then 100 ml of ethyl acetate was gradually added thereto and the mixture was further stirred at room temperature for 15 hours. Water was added to the reaction liquid and the separated insolubles were filtered off through a Celite layer. The resulting organic phase was washed with water, dried over anhydrous magnesium sulfate and then concentrated. The resulting residue was subjected to silica gel column chromatography treatment and eluted with chloroform/ethyl acetate (99/1) to give 0.95 g (yield 98.1%) of the title compound.

Provenance & Evidence