N-(2-(p-bromophenoxy)ethyl)pyrrolidine → HCID 21862737, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6.75 g (0.025 moles) of 1-(2-(4-bromophenoxy)ethyl)pyrrolidine in 250 ml of ether was cooled to −78° C. under N2. Several ml of THF were added to maintain a clear solution. 16.7 ml of 1.6 M n-butyllithium was added dropwise keeping the temperature below −70° C. After stirring at −78° C. for 1 hour, a solution of 5 g (0.024 moles) of 6,7-dimethoxy-1-tetralone in 25 ml of THF was added dropwise during 1 hour keeping the temperature below −70° C. After stirring for 2.5 hours at −78° C., the reaction was quenched by addition of 100 ml of 2N HCl. The reaction was allowed to warm to room temperature and the pH was adjusted to 7 by addition of 5N NaOH. The Et2O layer was separated and the aqueous layer was extracted 2 times with EtOAc. The combined Et2O/EtOAc layers were dried over Na2SO4 and evaporated to give 9 g of crude product, which was purified on 400 g of silica gel eluting with 95/5 CH2Cl2/MeOH to remove starting tetralone then with 85/15 CH2Cl2/MeOH to give 3.3 g of product.

Provenance & Evidence