Methyl Isocyanate → HCID 67606947, compound

Participants

Reaction Steps

A solution of amine 84 (220 mg, 0.4 mmol) in DCM (10 mL) was treated with TEA (0.11 mL, 0.78 mmol) followed by methyl isocyanate (0.05 mL, 0.78 mmol). After 2.5 h, the reaction mixture was quenched with MeOH (5 mL) followed by NH4OH (15M, 10 drops). After 10 min, the solution was diluted with DCM, washed successively with 1M HCl, saturated aqueous NaHCO3, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 90 as a pale, yellow-colored foam (175 mg, 72%) that was used without further purification. 1H NMR (CDCl3, 300 MHz): δ7.05 (q, J=9.0, 18.3 Hz, 1H), 6.89 (br s, 1H), 6.74-6.67 (m, 1H), 6.60-6.54 (m, 1H), 4.68 (br s, 1H), 4.61 (d, J=9.3 Hz, 1H), 4.51-4.48 (m, 1H), 4.40 (d, J=6.0 Hz, 1H), 4.25-4.22 (m, 1H), 4.08-3.99 (m, 2H), 3.79 (t, J=9.0 Hz, 1H), 3.58-3.55 (m, 1H), 3.47-3.34 (m, 2H), 2.84-2.79 (m, 7H), 2.42-2.36 (m, 1H), 2.13-2.00 (m, 1H), 1.70 (br s, 1H), 1.49 (s, 9H), 1.32 (d, J=6.9 Hz, 3H), 0.98 (s, 9H) ppm.

Provenance & Evidence