Hydrochloric Acid → (1S,2S,4S)-2,4-dimethylcyclohexanecarboxylic acid

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Reaction Conditions

Reaction Steps

A solution of (S,E)-4-benzyl-3-but-2-enoyloxazolidin-2-one (34.5 g, 0.14 mol) and isoprene (250 mL) in DCM was cooled to −78° C. To this solution was added a solution of Et2AlCl in toluene (100 mL, 0.18 mol) dropwise. The solution was warmed to −40° C. and stirred at this temperature overnight. 2 N HCl solution (150 mL) was added. Most of the DCM was removed under vacuum and the mixture was extracted with ether. After drying over Na2SO4, the combined organic layer was concentrated and the residue purified by silica gel chromatography (0-30% EtOAc in hexanes) to give the desired product (39 g, 88% yield) as a crystalline white solid.

Provenance & Evidence