Diisopropylethylamine → 1,1,1-trifluoro-3-[4-(4-nitrophenyl)-3,6-dihydropyridin-1(2H)-yl]propan-2-ol

Participants

Reaction Conditions

Reaction Steps

1,2-Epoxy-3,3,3-trifluoropropane, tech., 85% (2.32 g; 17.63 mmol; 1.20 eq.) was added to a suspension of 4-(4-nitrophenyl)-1,2,3,6-tetrahydropyridine (3.0 g; 14.7 mmol; 1.0 eq.) in DMF (60 mL) and DIEA (2.5 mL, 14.7 mmol, 1 eq.). The reaction mixture was heated at 45° C. for 4 h. It was then allowed to cool down to RT and diluted with water (50 mL) and EtOAc (100 mL). Organic layer was washed with a saturated solution of NH4Cl (2×50 mL) and water, dried over magnesium sulfate, filtered and concentrated to give the expected compound as an orange solid (3.6 g, 77%). UPLC/MS: (MS+) 317.3, (MS−) 315.3.

Provenance & Evidence