Trimethylsilyl isocyanate → HCID 54145025, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the (-)-trans-1,2,3,4,4a,5,6,10b-octahydro-10-bromo-4-(methylphenyl)benzo[f]quinoline (B-8, 6.60 g, 18.5 mmol) in dry tetrahydrofuran (50 mls) under nitrogen was cooled to -78° C., and t-bulyllithium (1.7M in pentane, 22.3 mls, 38.1 mmol) was added in about 10 seconds. The mixture was stirred at -78° C. for 5 minutes, and trimethylsilylisocyanate (46.5 mmol) was added via a syringe in one shot. The cold bath was removed, and the mixture was stiffed at ambient temperature for 1.5 hours. Water (30 mls) was added, and the mixture was stiffed for 10 minutes. Hydrochloiric acid (10%, 10 mls) was added, and file mixture was stiffed for 30 minutes. The mixture was bascified with 15% NaOH and extracted 3 times with methylene chloride. The extracts were dried (MgSO4), and the solvent was removed under vacuum to leave a white solid containing solvent (10.76 g). A sample (0.52 g) was crystallized from acetonitrile (20 mls) to yield the title compound (-) B-9 as white crystals (0.21 g, m.p. 189°-190° C., [α]D =-183.7° (25° C., THF, C=0.705)).

Provenance & Evidence