Potassium Hydroxide → 3-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)propanoic acid

Reaction equation

[OH-].[K+].C([O:5][C:6](=[O:22])[CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)C>O.CCO>[C:18]([O:17][C:15]([N:12]1[CH2:13][CH2:14][CH:9]([CH2:8][CH2:7][C:6]([OH:22])=[O:5])[CH2:10][CH2:11]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

Procedure

A solution of KOH (86%, 0.42 g, 6.4 mmol) in water (1.5 mL) was added to a solution of 3-(1-(tert-butoxycarbonyl)piperidin-4-yl)propionic acid ethyl ester in 95% EtOH (15 mL) at rt. After 2.5 h, the mixture was partitioned between EtOAc (50 mL) and 2 N aq. HCl (50 mL). After extraction of the aqueous layer with EtOAc (50 mL), the organic layers were washed with sat'd NaCl (25 mL), dried (Na2SO4), decanted, and evaporated to give 1.06 g of the title compound as a crystalline solid.