Ethyl 4-oxocyclohexanecarboxylate → HCID 89924053, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-iodopyrimidine (5 g, 17.55 mmol) was dissolved in dry toluene (90 mL) and cooled to −50 to −60° C. in a dry ice/acetone bath. n-Butyllithium (2.5M solution in hexanes, 7.3 mL) was added dropwise, and the reaction mixture was aged for 20 minutes. A solution of ethyl 4-oxocyclohexanecarboxylate (2.99 g, 17.55 mmol) in toluene (10 mL) was added in one portion, and the reaction mixture was allowed to warm to r.t. and stirred for 30 minutes. The reaction mixture was quenched with water (50 mL) and extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under vacuum. The resulting crude brown oil (6 g) was purified by chromatography on silica (Biotage, 100 g cartridge), eluting with a gradient of 0-50% ethyl acetate in heptanes, to afford a mixture of diastereoisomers of the title compound (2.99 g, 51%) as a yellow oil. Method C HPLC-MS: MH+ m/z 330, RT 1.32, 1.36 minutes.

Provenance & Evidence