Sodium Hydroxide → (3S)-1-((tert-butoxy)carbonyl)piperidine-3-carboxylic acid

Participants

Reaction Steps

Ethyl 1-(t-butoxycarbonyl)piperidine-3(S)-carboxylate (35.9 g, 0.099 mol) was dissolved in abs EtOH (70 mL), treated with 0.5N NaOH (418 mL, 0.209 mol), and heated at reflux for 0.75 h. The reaction mixture was cooled and extracted with EtOAc. The aqueous basic layer was cooled with ice, carefully acidified (pH 3) with 3N HCl and extracted with CH2Cl2 (3×100 mL). The organics were combined, dried (MgSO4), filtered, and concentrated to give the title compound.

Provenance & Evidence