Water → Ethyl (1S,3R,4S)-4-azido-3-[(tert-butoxycarbonyl)amino]cyclohexane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Sodium azide (357.6 mg) and tetrahexylammonium chloride (323.8 mg) were added at room temperature to a solution (2 mL) of ethyl (1S,3R,4R)-3-[(t-butoxycarbonyl)amino]-4-methanesulfonyloxycyclohexanecarboxylate (1.01 g) in N-methyl-2-pyrrolidone, followed by stirring at 60° C. for 74 hours. Water and ethyl acetate were added to the reaction mixture, and the organic layer was washed with aqueous saturated sodium bicarbonate solution and water, followed by drying over magnesium sulfate anhydrate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (n-hexane ethyl acetate=4:1), to thereby yield 712.2 mg of the title compound. Spectral data of this compound were found to be identical with those of the compound of Example 5.

Provenance & Evidence