HCID 20353247, compound → HCID 20353266, compound

Participants

Reaction Steps

To a suspension of 0.5 g of lithium aluminum hydride in 25 ml of ether was added dropwise a solution of 2.3 g of 5-acetyl-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]-pyrrole in 10 ml of ether. The reaction mixture was heated at reflux overnight and then excess lithium aluminum hydride was destroyed by the dropwise addition of a saturated aqueous sodium sulfate solution. The suspension was filtered with the aid of diatomaceous earth, and the filtrate was evaporated to dryness. The residue was dissolved in methylene chloride, and the solution was washed with water, dried over potassium carbonate and concentrated in vacuo to give 1.4 g of 5-(α-hydroxyethyl)-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole as an oil; nmr spectrum; δ 1.0-4.0 (m, 19); 1.3 (d, 3); 3.0-4.0 (m, 1); 4.7 (t, 1); 6.8-7.4 (m, 7).

Provenance & Evidence