(Bis(2-methoxyethyl)amino)sulfur trifluoride → 4-azidomethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

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Reaction Steps

To a solution of cis (±)-4-azidomethyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (1.95 mmol, 0.5 g) was added bis(2-methoxyethyl)aminosulfur trifluoride (2.34 mmol, 0.52 g) slowly and stirred for 12. The reaction mixture was diluted with DCM (10 mL), washed with aq. NaHCO3 solution, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography using ethyl acetate:hexanes (2:8) to get 4-azidomethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester.

Provenance & Evidence