1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 4-[2-(1-tert-Butoxycarbonyl-piperidin-4-yl)-2,3-dihydro-furo[2,3-c]pyridin-5-yl]-piperazine-1-carboxylic acid benzyl ester

Participants

Reaction Conditions

Reaction Steps

4-(5-Chloro-2-methyl-2,3-dihydro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (530 mg) is added to a mixture of piperazine-1-carboxylic acid benzyl ester (460 μL), Pd2(dba)3 (360 mg), Xantphos (700 mg), and potassium tert-butylate (270 mg) in toluene (16 mL) under an argon atmosphere. The reaction mixture is stirred in an oil bath at 105° C. for 4 h. The reaction mixture is concentrated in vacuo and chromatographed on silica gel (cyclohexane/ethyl acetate 70:30→35:65) to give the title compound. LC (method 10): tR=1.68 min; Mass spectrum (ESI+): m/z=523 [M+H]+.

Provenance & Evidence