N-bromobutanimide → Isohexane ethyl acetate

Participants

Reaction Steps

1-(4-Pyridyl)-3-(t-butyldimethylsilyloxy)pyrrolidine (8.92 g, 32.1 mmol) was dissolved in acetonitrile (140 ml) and N-bromosuccinimide (6.00 g, 33.7 mmol) was added portionwise. After stirring overnight the solvent was removed under reduced pressure and the residue partitioned between dichloromethane and water. The organic layer was dried over sodium sulphate. After evaporation of the solvent, the residue was purified by column chromatography on silica gel, eluting sequentially with CH2Cl2; 5%MeOH CH2Cl2; 10%MeOH/CH2Cl2. Further purification by column chromatography on alumina, eluting sequentially with isohexane; 25%EtOAc/isohexane gave the product as a colourless oil.

Provenance & Evidence