Binap, (A+-)- → (2R,4S)-4-[5-(4-Tert-butoxycarbonylbutoxy)pyrimidin-2-yl-amino]-2-ethyl-6-trifluoromethyl-1,2,3,4-tetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

5-(2-Chloropyrimidine-5-yloxy)-pentanoic acid tert-butyl ester (464 mg), palladium acetate (26 mg), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (81 mg) were dissolved in toluene (0.5 ml) and the mixture was stirred under nitrogen atmosphere at 50° C. for an hour. The reaction mixture was cooled to room temperature, thereto was added the compound obtained in Example 4 (1) dissolved in toluene (9.5 ml) and stirred at room temperature for 15 minutes. Then, sodium tert-butoxide (310 mg) was added and the mixture was stirred at room temperature for 4 days. Water and ethyl acetate was added to the mixture and the organic layer was separated, washed with a saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel; hexane:ethyl acetate=49:1→17:3→4:1) to give the titled compound (537 mg). MS (m/z): 495 [M+H]+.

Provenance & Evidence