Tetrahydrofuran → 4-(4-Carboxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1816332

Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22]C)=[O:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([OH:22])=[O:21])=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A solution of tert-butyl-4-[4-(methoxycarbonyl)phenyl]-1-piperidinecarboxylate (3.95 g) in a mixture of methanol (80 ml), THF (40 ml) and 4N sodium hydroxide (30 ml) was stirred at 80° C. for 2 hours. The reaction mixture was concentrated in vacuo. To a residue was added water (100 ml) and adjusted to pH 3 with 1N hydrochloric acid. The solution was extracted twice with a mixture of ethyl acetate (100 ml) and THF (50 ml). The extracts was dried over magnesium sulfate and evaporated in vacuo to give 4-[1-(tert-butoxycarbonyl)-4-piperidyl]benzoic acid (3.64 g).

Aufarbeitung

concentrationThe reaction mixture was concentrated in vacuo
additionTo a residue was added water (100 ml)
extractionThe solution was extracted twice with a mixture of ethyl acetate (100 ml) and THF (50 ml)
dry with materialThe extracts was dried over magnesium sulfate
customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-f26f4bb6040f4f4ba3c09e76e8fe6148
Quelldatensatz: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06884774B2

Verknüpfte Notizen

Wird geladen…