Acetic Acid → Methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-[(1Z)-3-(4-morpholinyl)-1-propen-1-yl]benzoate

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Reaction Steps

To a solution of methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-[(1Z)-3-oxo-1-propen-1-yl]benzoate (may be prepared as described in Description 122; 163 mg, 0.52 mmol) in 1,2-dichloroethane (10 ml) was added morpholine (0.05 ml, 0.52 mmol) and acetic acid (0.03 ml, 0.52 mmol). The solution was stirred for 3 hours then sodium triacetoxyborohydride (165 mg, 0.78 mmol) was added and stirred for one hour. Saturated NaHCO3 solution (10 ml) was added and the mixture was stirred for 15 minutes. Dichloromethane (10 ml) was added and the organic layer was separated, dried (MgSO4) and the solvent removed in vacuo to yield the title compound as a yellow gum. 197 mg.

Provenance & Evidence