CAS: 74103-06-3; 5-Benzoyl-2,3-Dihydro-1H-Pyrrolizine-1-Carboxylic Acid

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Methyl Isopropyl 5-Benzoyl-1,2-Dihydro-3H-Pyrrolo<1,2-A>Pyrrole-1,1-Dicarboxylate置于sodium Hydroxide体系中,用 甲醇 作为反应溶剂,以99%的收率获得产物酮咯酸
参考文献:Highly Efficient Synthesis Of Alkyl Pyrrolylacetates And Dialkyl Pyrrolylmalonates
标题:Highly Efficient Synthesis Of Alkyl Pyrrolylacetates And Dialkyl Pyrrolylmalonates
摘要:N-Pyrrolylmagnesium Halides (1,2) React With Alkyl Bromoacetates (3A-D) In Thf Solution To Give Alkyl 2-Pyrrolylacetates (5A-D) In Good Yields And With Very High Positional Selectivity (C-2:C-3 Greater Than Or Equal To 25). The High Regioselectivity Is Rationalized In Terms Of An Increased Propinquity Between C-2 And The Bromoacetate Methylene Group As A Consequence Of Coordination Between Magnesium And The Carbonyl Oxygen Of The Alkylating Agent,(2,5-Dimethylpyrrol-N-yl)Magnesium Chloride (9) And Isopropyl Bromoacetate (3C) Gave The 3-Pyrrolylacetate 10 Exclusively. Alkoxycarbonylation Of The Dianions Of The Above Alkyl Pyrrolylacetates With Alkyl Chloroformates Gave The Corresponding Dialkyl Pyrrolylmalonates,Two Of Which (16A And 19) Were Transformed Into The Dialkyl 1,2-Dihydro-3H-Pyrrolo[1,2-A]Pyrrole-1,1-Dicarboxylates (22 And 20,Respectively) With 1,2-Dichloroethane Under Phase Transfer Conditions. Compound 20 Was Converted Into The Powerful Nonaddicting Analgesic Ketorolac (21).
DOI:10.1021/jo00097A025