Sodium Hydroxide → 4-[4-(1-Carboxy-ethyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 409725Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To 3.30 g (9.50 mmol) 4-[4-(1-methoxycarbonyl-ethyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester (VIII.1) in 20 mL MeOH are added 10.5 mL (10.5 mmol) 1N NaOH solution and the mixture is stirred at 70° C. for 1 h. After that time, the solvent is evaporated and the residue is washed with DCM. The residue is taken up in 1N HCl and the precipitate is filtered off and dried in vacuo to yield the desired product.

Workup

customAfter that time, the solvent is evaporated
washthe residue is washed with DCM
filtrationthe precipitate is filtered off
customdried in vacuo

Sources & evidence

ORD record: ord-a4bf24768bbc492bb00d461af6ecc471
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759528B2

Reaction notes

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