Sodium Hydroxide → (2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

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Reaction Steps

1N NaOH (1.2 ml, 1.2 mmol, 1.2 eq) was added to a stirred solution of (R)-1-tert-butyl 2-methylpyrrolidine-1,2-dicarboxylate (0.267 g, 1.0 mmol, 1 eq) in 4 ml of 3:1 THF/MeOH. After stirring overnight the solvent was removed in vacuo. The residue was dissolved in saturated aqueous NaHCO3 and extracted with Et2O (×2). The aqueous layer was adjusted to pH {tilde over ( )} 4 with 1N HCl and extracted with EtOAc (×4). The combined EtOAc fractions were dried over Na2SO4. The inorganics were filtered off, and the solvent removed in vacuo yielding 0.1615 g (0.64 mmol, 64% yield) of (R)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid.

Provenance & Evidence