Methane → 2-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid

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Reaction Steps

A solution of racemic 2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester (Intermediate 1) in 400 mL 10% NaOH and 80 mL ethanol was refluxed for 6 hours. The solution was allowed to cool, treated with decolorizing charcoal, and filtered thru supercel. The ethanol was evaporated at reduced pressure and the residual solution was cooled in an ice bath and acidified with concentrated HCl to pH 1. The product precipitated and was granulated for one hour, then collected by filtration to give 2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid as a white solid (19.38 g, quantitative).

Provenance & Evidence