Trimethylsilyl isocyanate → HCID 15703613, compound

Participants

Reaction Steps

A solution of (R)-2-(dipropylamino)-7-bromo-1,2,3,4-tetrahydronaphthalene (7) (13.02 g) in dry tetrahydrofuran was cooled to -78° C. t-Butyllithium (1.7 M in pentane, 50.6 ml) was added via syringe over a period of 6 minutes, and the mixture was stirred for an additional 8 minutes. Trimethylsilylisocyanate (13.4 ml, 85% pure, 84.1 mmol) was added in one dose, and the mixture stirred at -78° C. for 10 minutes and at room temperature for 1.5 hours. The reaction mixture was quenched with 10% hydrochloric acid, and after stirring for 30 minutes, it was basified with 15% sodium hydroxide. The free base was extracted with diethylether and 1:1 tetrahydrofuran/diethylether. The combined extracts were washed with brine and dried (MgSO4). The solvent was removed under vacuum to leave an oil (15.25 g). Crystallization from ethyl acetate/hexane gave off-white crystals (6.30 g), m.p. 132-132° C. [α]D =+67° (25° C., CH3OH, c=0.8139).

Provenance & Evidence