2-(Dimethylamino)ethanol → HCID 59541938, compound

Participants

Reaction Conditions

Reaction Steps

Into a solution of 4-(4-hydroxy-phenyl)cyclohexanone (as prepared in Example 40, Step E, 2.4 g, 12.6 mmol), N,N-dimethylethanolamine (Aldrich, 3.37 g, 37.8 mmol) and triphenylphosphine (Aldrich, 9.91 g, 37.8 mmol) in THF (100 mL) at 0° C. was added dropwise a solution of diisopropyl azodicarboxylate (7.44 mL, 37.8 mmol) in THF (15 mL) under Ar. The resulting solution was stirred at 0° C. for 1 h and at room temperature overnight. The solvent was removed and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate concentrated in vacuo to give a colorless oil, which was purified on a silica gel column by a CombiFlash® system using hexanes and ethyl acetate as eluent (from pure hexanes to pure ethyl acetate) to afford the title compound as a white solid.

Provenance & Evidence