1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59840700, compound

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Reaction Steps

A 25 mL flask was charged with (2-methyl-6-(trifluoromethyl)pyridin-3-yl)methanol (287 mg, 1.50 mmol), tetrahydrofuran (5 mL) and diphenylphosphonic azide (356 μL, 1.65 mmol), purged with nitrogen, and cooled in ice. A solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (236 μL, 1.57 mmol) in THF (1 mL) was added dropwise to the resultant mixture, and after 1.5 h, the mixture was warmed to room temperature and stirred overnight. Additional diphenylphosphonic azide (100 μL, 0.3 equiv.) was added followed by additional 1,8-diazabicyclo[5.4.0]undec-7-ene (90 μL, 0.4 equiv.), and the mixture was again stirred overnight. The reaction was quenched with 1M NaOH (20 mL), and poured into chloroform (20 mL). The organic layer was washed with 1M Na2HPO4 (pH 8, 2×15 mL), dried (Na2SO4), filtered and concentrated to a yellow oil which was purified by silica gel column (0-25% ethyl acetate/hexane) to yield a colorless oil (301 mg, 93%).

Provenance & Evidence