Sulfuric Acid → HCID 86702283, compound

Participants

Reaction Conditions

Reaction Steps

Under nitrogen atmosphere, tetrahydrofuran (1.6 ml) and acetonitrile (0.4 ml) were added to (2S)-5-benzyloxyimino-piperidine-2-carboxylic acid dibenzylamide (0.214 g, 0.50 mmol), and the obtained mixture was cooled down to −10° C. Sulfuric acid (0.302 g, 3.06 mmol) was added to the mixture, and then sodium borohydride (0.0757 g, 2.00 mmol) was added. After 22 hours of stirring, ethyl acetate (10 ml) and water (5 ml) were added to the mixture, the pH of the mixture was adjusted at 11 with 30% by weight sodium hydroxide aqueous solution, and the obtained mixture was separated. The organic layer was dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 0.176 g of the title compound (yield: 82%). The diastereo selectivity was (2S,5R)/(2S,5S)=87.7/12.3 (75.4% de).

Provenance & Evidence