HCID 70983650, compound → HCID 70983672, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-methyl-4-(1,3-thiazol-2-ylcarbonyl)cyclohexanecarboxylate (2.8 g, 10 mmol) in THF (28 mL) at −40° C. was added MeMgBr (3.0 M in THF, 4.0 mL, 12 mmol) at such a rate the internal temperature did not exceed −30° C. The reaction mixture was stirred for 15 minutes at −40° C., and was then quenched with saturated aqueous ammonium chloride (50 mL) and warmed to room temperature. EtOAc (20 mL) was added, the layers separated, and the aqueous layer was extracted a second time with EtOAc (50 mL). The organic layers were combined, dried over MgSO4, filtered, absorbed on silica, and purified by silica gel chromatography to afford ethyl 4-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]-2-methylcyclohexanecarboxylate.

Provenance & Evidence