反应详情

The mixture of cis-4-tert-butylcyclohexanol (30.4 mg, 0.000195 mol), (R)-4-(6-hydroxy-5-(trifluoromethyl)naphthalen-2-yl)-4-methyloxazolidin-2-one (50.5 mg, 0.000162 mol) and triphenylphosphine (51.1 mg, 0.000195 mol) in tetrahydrofuran (2 mL, 0.02 mol) was heated to reflux, and diisopropyl azodicarboxylate (0.0383 mL, 0.000195 mol) was is added dropwise and was stirred and refluxed for 3 hours. The mixture was taken up into methylene chloride and subjected to chromatography purification with EtOAc/hexane (10:90 to 80:20) to give product (R)-4-(6-(trans-4-tert-butylcyclohexyloxy)-5-(trifluoromethyl)naphthalen-2-yl)-4-methyloxazolidin-2-one (22.2 mg, 30%). LCMS: Rf=2.41 min (450.46, M+1, 70%; 491.47, M+ACN, 100%). 1H NMR (400 MHz, CHLOROFORM-d) δ=8.25 (dd, J=8.7, 1.4 Hz, 1H), 7.91 (d, J=9.0 Hz, 1H), 7.79 (d, J=2.0 Hz, 1H), 7.52 (dd, J=9.3, 2.3 Hz, 1H), 7.34 (d, J=9.3 Hz, 1H), 5.98 (br. s., 1H), 4.45 (d, J=8.6 Hz, 1H), 4.41 (d, J=8.6 Hz, 1H), 4.38-4.26 (m, 1H), 2.19 (d, J=13.1 Hz, 2H), 1.89 (d, J=10.0 Hz, 2H), 1.87 (s, 3H), 1.59-1.48 (m, 2H), 1.21-1.05 (m, 3H), 0.89 (s, 9H).

1. temperaturewas heated
2. temperatureto reflux
3. temperaturerefluxed for 3 hours
4. customsubjected to chromatography purification with EtOAc/hexane (10:90 to 80:20)