Ammonium Chloride → Dimethyl 7-(3-bromophenyl)-3-oxo-9-azabicyclo[3.3.1]nonane-2,4-dicarboxylate

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Reaction Steps

3-(3-Bromophenyl)pentanedial (87), dimethyl 3-oxopentanedioate (88) (5.78 g, 33.2 mmol), ammonium chloride (14.42 g, 270 mmol) in THF (100 ml), 10% aqueous HCl (100 ml), and water (100 ml) was stirred for 18 h. Sodium acetate was then added until the pH was 4-5. After stirring for 6 h, the solution was extracted with EtOAc. The combined organic extracts were washed with saturated aqueous Na2CO3, dried over MgSO4, filtered and concentrated to afford compound 89.

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