Water → HCID 19839071, compound

Participants

Reaction Steps

A solution of 344 g of cerium(IV) ammonium nitrate in 1.1 1 of acetonitrile is added dropwise to a stirred solution of 53 g of 3-(4-methoxybenzyl)-1-phenyl-3-azabicyclo[3.1.1]heptane-2,4-dione in 560 ml of acetonitrile at room temperature. After 1 hour, 515 ml of water are added and the mixture is stirred for 2 hours. It is concentrated to half the volume by distilling off the acetonitrile and is then diluted with 1 1 of water. The product which has precipitated is filtered off with suction, washed with water and dried in vacuo. The brown-yellowish crystalline substance is taken up in 800 ml of methylene chloride, 11 ml of n-propylamine are added and the mixture is left to stand overnight. The black solution is concentrated and 80 ml of methylene chloridediethyl ether (1:1) are added to the brown crystalline mass, and the crystals are filtered off with suction and dried under a high vacuum. The title compound is obtained as white crystals of m.p. 217-218° C.

Provenance & Evidence