Practical synthesis of Boc-protected cis-4-trifluoromethyl and cis-4-difluoromethyl-L- prolines.
A short, efficient, and diastereomerically pure synthesis of N-Boc-cis-4-trifluoromethyl-L-proline (7) and N-Boc-cis-4-difluoromethyl-L-proline (9) from N-Boc-4-oxo-L-proline (4) is described. The reaction of 4 with Me(3)SiCF(3) and the conversion of the carbonyl group of 4 into the difluoromethylene group are the key steps for the synthesis of 7 and 9, respectively.
D002851:Chromatography, High Pressure Liquid; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
C472230:N-tert-butoxycarbonyl-4-difluoromethylproline; C472229:N-tert-butoxycarbonyl-4-trifluoromethylproline; C472228:benzyl N-tert-butoxycarbonyl-4-oxo-prolinate; D011392:Proline