Acetic Acid → HCID 178472457, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 4-oxo-cyclohexanecarboxylate (1.00 g, 5.88 mmol), tert-butyl hydrazinecarboxylate (1.16 g, 8.81 mmol) and acetic acid (0.34 ml, 5.9 mmol) in dichloromethane (29 ml) was stirred for 1 h at room temperature and subsequently cooled to 0° C. on an ice-water bath. Sodium triacetoxyborohydride (2.49 g, 11.8 mmol) was added at 0-5° C. The cooling bath was removed after completed addition. Stirring at room temperature for 20 h was followed by quenching with ethanol (5 ml). The reaction mixture was washed with one 50-ml portion of water. The aqueous layer (pH 4) was extracted with two 50-ml portions of dichloromethane. The combined organic layers were washed with one 50 ml-portion of aqueous 2 M sodium carbonate solution, dried over anhydrous sodium sulfate and concentrated in vacuo. Flash-chromatography with n-heptane/ethyl acetate as eluent gave cis-4-(N′-tert-butoxycarbonyl-hydrazino)-cyclohexanecarboxylic acid ethyl ester (1.05 g, 62%) and trans-4-(N′-tert-butoxycarbonyl-hydrazino)-cyclohexanecarboxylic acid ethyl ester (0.63 g, 37%).

Provenance & Evidence