合成路线:Optical resolution of DL-pipecolinic acid (I) with (+)-tartaric acid gives L-pipecolinic acid (II),which is treated with PCl5 to obtain acil chloride (III).This compound is condensed with 2,5-dimethylaniline (IV) by means N-methylpirrolidine (NMP) to afford amide (V).Finally,amide (V) is alkylated with 1-bromopropane by means potassium carbonate (K2CO3) to yield Ropivacaine.
合成路线:L-Picolinic acid (II) is protected with benzyl chloroformiate (VII) to afford compound (VIII),which is condensed with 2-methylaniline (IX) by means SOCl2/DMAP to yield amide (X).This compound (X) is methylated by treatment with palladium acetate (Pd(Oac)2) to obtain compound (XI),which is deprotected by means HBr to yield compound (V).Finally,this compound (V) is alkylated with 1-iodopropane by means potassium carbonate (K2CO3) to yield Ropivacaine.
合成路线:Compound (XII) is protected with benzyl chloroformiate (VII) to afford compound (XIII),which is condensed with 2,5-dimethylaniline (XIV) by means SOCl2/DMAP to yield amide (XIV).This compound (XIV) is deprotected by means trimethylsillyl chloride to yield compound (XV),which is hydrogenated by means Rh/Al2O3.Finally,this compound (V) is alkylated with 1-iodopropane by means potassium carbonate (K2CO3) to yield Ropivacaine.
参考文献标题:S-(-)-1-propyl-2',6'-pipecoloxylidide hydrochloride monohydrate,process for its preparation and pharmaceutical preparation containing it
文献作者:Sandeberg,R.V.(AstraZeneca plc)
参考来源:EP 0239710; US 4870086
产品链接: CAS No. 84057-95-4››