1-(1H-benzimidazol-2-ylmethyl)-6-benzyl-octahydro-quinolin-2-one → 1-(1H-benzimidazol-2-ylmethyl)-6-benzyl-decahydro-quinoline

Participants

Reaction Steps

A stirred solution of 0.15 g of 1-(1H-benzimidazol-2-ylmethyl)-6-benzyl-octahydro-quinolin-2-one in 20 mL of dry THF containing 0.1 g of lithium aluminum hydride was heated to reflux overnight, cooled in an ice bath, and quenched with 0.1 mL of 5N NaOH, then 1 mL of water. After stirring and warming to room temperature for 2 h, the mixture was filtered through a glass frit and the filtrate concentrated to dryness under reduced pressure. Chromatography using 10% methanol in chloroform gave 1-(1H-benzimidazol-2-ylmethyl)-6-benzyl-decahydro-quinoline in four bands.

Provenance & Evidence