1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → HCID 10139659, compound

Participants

Reaction Conditions

Reaction Steps

A mixture that consists of 42.1 g (100 mmol) of 2,3,5-tri-O-benzyl-ribofuranose, 3.40 g (10 mmol) of tetrabutylammonium hydrogen sulfate and 33.7 g (600 mmol) of fine-powder potassium hydroxide in 3050 ml of benzene is cooled to 10° C. At 10° C., 38.1 g (150 mmol) of N-(2-bromoethyl)-phthalimide, dissolved in 100 ml of benzene, is added in drops over 40 minutes while being stirred vigorously. It is stirred for three hours at 10° C. 300 ml of benzene is added, solid is filtered out, and the filtrate is evaporated to the dry state in a vacuum. The filtrate residue is dissolved in 500 ml of ethanol, 25.03 g of hydrazine hydrate (500 mmol) is added, and it is refluxed for six hours. It is allowed to cool to 0° C., deposited precipitate is filtered out, and the filtrate is evaporated to the dry state in a vacuum. The residue is dissolved in 400 ml of dichloromethane, and this solution is washed twice with 5% aqueous sodium hydroxide solution and then once with water (in each case 300 ml). The organic phase is evaporated to the dry state in a vacuum, and the residue is chromatographed on silica gel (mobile solvent: dichloromethane/ethanol/triethylamine=20:2:0.1).

Provenance & Evidence