1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18475857, compound

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Reaction Steps

To a stirred solution of 1-(4-cyano-3-fluorobenzyl)-5-(hydroxymethyl)imidazole, as described above in Example 4, Step F, (103 mg, 0.45 mmol) in dry THF (1 mL), at 0° C., under argon, were added DPPA (147 mg, 0.53 mmol) then DBU (75 mg, 0.49 mmol). The mixture was allowed to warm to ambient temperature and then stirred for 3 hrs. The mixture was then partitioned between H2O (10 mL) and CH2Cl2 (20 mL). The aqueous layer was extracted further with CH2Cl2 (2×15 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with a gradient of CHCl3-1% MeOH −0.1% NH4OH to CHCl3-5% MeOH −0.5% NH4OH, to yield the titled product.

Provenance & Evidence