Sodium hydride → (4aR*,8aR*)-2-oxo-octahydro-pyrido[3,4-b][1,4]oxazine-6-carboxylic acid tert-butyl ester

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Reaction Steps

To a stirring solution of (3R*,4R*)-4-(2-chloro-acetylamino)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (2.70 g, 9.23 mmol) in tetrahydrofuran (30 mL) cooled down to 0° C. was added sodium hydride, 60% dispersion in mineral oil (830 mg, 1.1 eq) portionwise. The mixture was warmed to room temperature and stirred for 6 hours. The mixture was partitioned between dichloromethane and brine. The combined organic layers were washed with brine, separated and dried (MgSO4). The crude product was purified by column chromatography to yield (4aR*,8aR*)-2-oxo-octahydro-pyrido[3,4-b][1,4]oxazine-6-carboxylic acid tert-butyl ester (1.31 g).

Provenance & Evidence