Phenyl isocyanate → HCID 59371321, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-nitro-2-(tetrahydro-2H-pyran-2-yloxy)ethane (Basra, S. K.; Drew, M. G. B.; Mann, J.; Kane, P. D. J. Chem. Soc., Perkin Trans. 1, 2000, 3592-3598) (0.53 mL, 3.4 mmol, 3.0 equiv.) and 3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-5-ethynylpyridine (330 mg, 1.14 mmol) in dry benzene (11 mL) were added phenyl isocyanate (0.37 mL, 3.4 mmol, 3.0 equiv.) and triethylamine (0.70 mL, 5.0 mmol, 4.4 equiv.). The reaction mixture was stirred at 60° C. for 24 h, then diluted with water, stirred vigorously for 2 h, and extracted with CH2Cl2. The combined organic phases were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by CC on SiO2 with EtOAc/hexane 1:1 to give the isoxazole (420 mg, 82%). 1H NMR (CDCl3, 400 MHz) δ 8.64 (br s, 1H), 8.41 (br s, 1H), 7.64 (s, 1H), 6.71 (s, 1H), 4.86 (d, 1H, J=12.0 Hz), 4.77 (t, 1H, J=4.0 Hz), 4.68 (d, 1H, J=12.0 Hz), 4.55 (m, 1H), 4.41 (m, 1H), 4.21 (dd, 1H, J=8.0, 4.0 Hz), 3.91 (t, 3H, J=8.0 Hz), 3.59 (m, 1H), 2.38 (m, 2H), 1.78 (m, 2H), 1.58 (m, 4H), 1.42 (s, 9H).

Provenance & Evidence