Sodium Hydroxide → 4-[3-(4-Carboxy-2-methyl-phenoxy)-propyl]-piperidine-1-carboxylic Acid Tert-butyl Ester

HRID 220897Notes

Reaction equation

[OH-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([O:28]C)=[O:27])=[CH:22][C:21]=2[CH3:30])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>O1CCOCC1>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH2:12][CH:13]([CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([OH:28])=[O:27])=[CH:22][C:21]=2[CH3:30])[CH2:14][CH2:15]1)=[O:9])([CH3:5])([CH3:6])[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

2M NaOH solution (1.25 ml, 2.5 mmol) was added to 4-[3-(4-methoxycarbonyl-2-methyl-phenoxy)-propyl]-piperidine-1-carboxylic acid tert-butyl ester from Example E68.2 (340 mg, 0.87 mmol) in dioxan (10 ml) and the mixture was heated at 60° C. for 20 h. 2M NaOH solution (5 ml, 10 mmol) was added and the mixture was heated at 60° C. for 20 h then concentrated in vacuo. The residue was purified by flash chromatography on silica gel through an isolute (eluant; 1% acetic acid:9% methanol:90% dichloromethane) to yield the title compound (303 mg, 92%).

Workup

temperaturethe mixture was heated at 60° C. for 20 h
concentrationthen concentrated in vacuo
customThe residue was purified by flash chromatography on silica gel through an isolute (eluant; 1% acetic acid:9% methanol:90% dichloromethane)

Sources & evidence

ORD record: ord-53932087ac79473e96ba5a0df1ef3912
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202858B2

Reaction notes

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