Sodium Bromide → Tert-butyl 3-oxopiperidine-1-carboxylate

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Reaction Steps

3-hydroxy-piperidine-1-carboxylic acid t-butyl ester (4.0 g, 20 mmol) synthesized in Section (1) was dissolved in a mixed solution (2:1:2, 100 mL) of toluene, water and ethyl ester, and 1.0 mol% TEMPO (31 mg), and NaBr (2.3 g) were sequentially added thereto. A mixture of NaHCO3 (4.7 g) and NaOCl (5%, 36 mL) was slowly added to the mixture under cooling conditions (0 to 4° C.). After the reaction was complete, the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtered organic layer was concentrated under reduced pressure to afford 3.8 g (yield: 95%) of the title compound.

Provenance & Evidence