반응 #159293

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product

3-chloro-7-methoxyquinoxalin-2-ol

Cs2CO3

1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate

1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate

→

title compound

수율 35.0%

1-tert-butyl 2-methyl (2S,4R)-4-[(3-chloro-7-methoxyquinoxalin-2-yl)oxy]pyrrolidine-1,2-dicarboxylate

수율 35.0%

용매

NMP

H2O

EtOAc

반응 조건

후처리

1. 1
   workup.STIRRINGAfter stirring for 2 hours
2. 2
   온도the mixture was cooled
3. 3
   세척The organic phases were washed with aqueous HCl (1 N), saturated aqueous NaHCO3 and brine
4. 4
   농축The dried organic phase was concentrated to a residue that
5. 5
   기타was purified by flash-chromatography (0-60% EtOAc/petroleum ether)

실험 절차

A solution (0.35M) of the product of step 2 in NMP was treated with Cs2CO3 (1.5 eq) and 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (1.1 eq). The resulting mixture was stirred at 50° C. for 18 hours, then a further portion (0.1 eq) of 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate was added. After stirring for 2 hours, the mixture was cooled and diluted with H2O and EtOAc. The organic phases were washed with aqueous HCl (1 N), saturated aqueous NaHCO3 and brine. The dried organic phase was concentrated to a residue that was purified by flash-chromatography (0-60% EtOAc/petroleum ether) to give the title compound (35% for two steps) as a solid. MS (ES−) m/z 438 (M+H)+

출처