Water → HCID 22813386, compound

Participants

Reaction Steps

A suspension of trans-4-(p-tolylsulphonyl)-4,6,6a,8,9,10a-hexahydro-7-methyl-7H-indolo-[3,4 gh]-[1,4]-benzoxazin-8-one (3.0 gms; 0.008 m) and lithium aluminum hydride (3.0 gm; 0.08 m) in tetrahydrofuran (200 ml) is refluxed for 17 hours. The cooled solution is hydrolyzed with water (6 ml). The solid is filtered, and the organic solvent is dried over anhydrous sodium sulfate. After filtration, the solvent is removed under reduced pressure (20 mm). The gum is crystallized from methanol (2-5 ml) to yield 420 mg of trans-4,6,6a,8,9,10a-hexahydro-7-methyl-7H-indolo-[3,4 gh]-[1,4]-benzoxazine. This solid is purified by chromatography (silica, CHCl3 /NH4OH) to give 330 mg of trans-4,6,6a,8,9,10a-hexahydro-7-methyl-7-H-indolo-[3,4 gh]-[1,4]-benzoxazine; m.p. 175°-177° (softening at 100°).

Provenance & Evidence