[CH3:1][CH:2]1[NH:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.Cl.[OH-].[Na+].[CH3:14][CH2:15]O>O>[CH3:1][CH:2]1[NH:7][CH2:6][CH:5]([C:8]([O:10][CH2:14][CH3:15])=[O:9])[CH2:4][CH2:3]1To 194.1 (1044 mg, 7.29 mmol) in EtOH (5207 μL) was added concentrated hydrochloric acid (405 μL, 7.29 mmol). The resulting solution was heated at reflux for 18 hours. The reaction mixture was then cooled to room temperature and poured onto water. The reaction was brought to pH 10 with 1N sodium hydroxide in water and was then extracted with EtOAc. The organic phase was then dried over anhydrous Na2SO4 and filtered to provide ethyl 6-methylpiperidine-3-carboxylate. ESI-MS M+H 172.2.
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