Dichloromethane → HCID 86735703, compound

Participants

Reaction Steps

To a stirred mixture of 5.0 g (13.6 mmoles) of 5-acetyl-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole, (Example 66), and 1.5 g (21.3 mmoles) of hydroxylamine hydrochloride in 25 ml of ethanol and 5.0 ml of water was added portionwise 2.8 g (70 mmoles) of powdered sodium hydroxide. The reaction mixture was then heated at reflux for 5 minutes, cooled, and distributed between water and methylene chloride. The organic layer was washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel CC No. 7 with 5% methanol in chloroform to give 1.3 g of 5-acetyl-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole oxime as an oil; nmr spectrum: δ 1.0-4.0 (m, 19); 2.2 (s, 2); 6.8-7.4 (m, 7); 7.5 (s, 1).

Provenance & Evidence