Hydrochloric Acid → (3S,4S)-1-((tert-Butoxy)carbonyl)pyrrolidine-3,4-dicarboxylic acid

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Reaction Steps

Compound 1b (1 g, 3.17 mmol) was dissolved in of THF (8 ml), and 80 mL of water was added. The reaction mixture was immersed in an ice-water bath and cooled to 0 C. To this reaction mixture, 96 ml of 0.25 N NaOH was added in small portions with stirring until the consumption of the starting diester was detected by thin-layer chromatography. The reaction was stirred at the same temperature for about 30 min to 1 h, and the reaction mixture was acidified with 1 N HCl at 0° C., saturated with NaCl, extracted with ethyl acetate four times (each 100 ml), and dried with sodium sulfate. The organic phase is evaporated to dryness and dried in vacuo. Yield: 0.68 g (82.7%), ESI-MS: m/z=258 [M−H]−

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