Hydrochloric Acid → HCID 178455365, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of trans-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexylamine (1.0 g, 4.36 mmol) (from Example 3a supra) and triethylamine (3.04 mL, 21.8 mmol) (Burdick & Jackson) in dichloromethane (30 mL) at 0° C. was added phosgene (˜20% in toluene, 6.4 mL, 13.1 mmol) (Fluka) in one portion. The reaction mixture was stirred at 0° C. for 40 minutes, followed by addition of 0.5N aqueous hydrochloric acid (50 mL). The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate-hexanes (1:9) to give tert-butyl-(trans-4-isocyanato-cyclohexyloxy)-dimethyl-silane. (Yield 0.90 g, 81%).

Provenance & Evidence