Water → HCID 68916190, compound

Participants

Reaction Steps

((S)-6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester (12.2 g, 37.4 mmol) was dissolved in N,N-dimethylformamide (1000 ml). Sodium hydride (50% in oil) (1.975 g, 41.14 mmol) was added and stirred for 15 minutes at room temperature. Propyl bromide (3.74 ml, 41.14 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into a mixture of ice and H2O (400 ml) and twice extracted with 200 ml diethyl ether. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness to yield 14.4 g of crude product. The crude product was purified with silica gel chromatography with cyclohexane/ethyl acetate (95:5) as eluent, yielding the purified product (10.5 g, 76%).

Provenance & Evidence