Benzene → HCID 20353269, compound

Participants

Reaction Steps

The above product (2.94 g) is treated with 1.41 g of bromine in methylene chloride at room temperature. The resulting crude 12b,13-dibromo-2-cyclohexylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrol-1-one is heated under reflux with 9 g of tributyltin hydride and 25 ml of anhydrous benzene for 3 days. The benzene is removed and the residue is concentrated further using short-path distillation (1 micron, 125° bath temperature). Crystallization of the residue from isopropyl alcohol gives 2.39 g of 2-cyclohexylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrol-1-one; nmr spectrum: τ 2.2-3.3 (m, 8); 5.9-6.2 (m, 2); 6.6-7.0 (m, 4); 8.1 (m, 2) and 8.1-9.7 (m, 11).

Provenance & Evidence