Hydrochloric Acid → 1-(tert-Butoxycarbonyl)-4-[(4-chlorophenyl)methyl]piperidine-4-carboxylic acid

HRID 2401542Notizen

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 4-(4-chlorobenzyl)piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (1.515 g, 4.117 mmol) in dioxane (20 ml), methanol (10 ml) and water (10 ml) at room temperature was added lithium hydroxide monohydrate (3.455 g, 82.341 mmol). After stirring at 50° C. for 2 days the solution was acidified to pH 6 with 2M HCl and the resulting white precipitate was extracted with diethyl ether (2×100 ml). The organic phases were combined, dried over sodium sulphate and concentrated to dryness, to give the acid as a white solid (1.460 g, 100%). LC-MS (LCT) m/z 376 [M+Na+], Rt 7.62 min.

Aufarbeitung

extractionthe resulting white precipitate was extracted with diethyl ether (2×100 ml)
dry with materialdried over sodium sulphate
concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag: ord-d21d275f413642a4b474bff07223ad8e
Quelldatensatz: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08796293B2

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