Hydrochloric Acid → HCID 178483639, compound

Participants

Reaction Steps

To 10.14 g (36.17 mmol) of trans-[2-(4-cyanomethyl-cyclohexyl)-ethyl]-methyl-carbamic acid tert-butyl ester in 90 mL of CH2Cl2 were added 90 mL (108.5 mmol, 3 eq) of 1.2M DIBAH at −70-−78° C. The solution was stirred at that temperature for 4 h, 40 mL of 4M HCl were added carefully and the solution was slowly warmed to RT. Stirring was continued at RT for 10 min, and the substance was partioned between ether and 1M HCl. The organic phases were washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography with n-hexane: EtOAc 1:3 to yield 7.5 g (73%) of trans-methyl-{2-[4-(2-oxo-ethyl)-cyclohexyl]-ethyl}-carbamic acid tert-butyl ester.

Provenance & Evidence