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To a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet were added 5.59 g (28.36 mmol) ethyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 142 mL ethanol, and 9.47 g (56.72 mmol) ethyl bromoacetate. The reaction was refluxed 3 days, cooled, and evaporated. The residue was partitioned between methylene chloride and aqueous sodium hydroxide, and the organic layer was dried over sodium sulfate and evaporated. The residue was filtered through silica gel using ethyl acetate to afford an oil, 4,835 g (100% yield crude), as a mixture of diastereomers.

1. customTo a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet
2. temperatureThe reaction was refluxed 3 days
3. temperaturecooled
4. customevaporated
5. customThe residue was partitioned between methylene chloride and aqueous sodium hydroxide
6. dry with materialthe organic layer was dried over sodium sulfate
7. customevaporated
8. filtrationThe residue was filtered through silica gel
9. customto afford an oil, 4,835 g (100% yield crude)
10. additionas a mixture of diastereomers