1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 10971697, compound

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Reaction Steps

To a solution of 6-tert-butyldiphenylsilyloxy-1-indanol, as described above in Step B, (5.80 g, 14.9 mmol) and diphenylphosphoryl azide (4.98 g, 18.1 mmol) in toluene (30 mL) at 0° C. was added 1,8-diazabicyclo[5.4.0]undec-7-ene (2.50 mL, 16.4 mmol), dropwise. The mixture was allowed to slowly warm to ambient temperature and was stirred for 18 hours, then washed with H2O (10 mL), then dilute HCl (10 mL), then dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with hexane—1% EtOAc, to yield the titled product.

Provenance & Evidence