Water → (1-Benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanol

HRID 914855

Reaktionsgleichung

[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][O:2]1.[CH2:10]([N:17]1[CH2:22][CH2:21][CH:20]([CH:23]=[O:24])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.C(OCC)(=O)C>O1CCCC1.C([Li])CCC>[CH2:10]([N:17]1[CH2:22][CH2:21][CH:20]([CH:23]([CH:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][O:2]2)[OH:24])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: -70 °C

Versuchsvorschrift

After dissolving 591 mg of 1,3-dihydroisobenzofuran in 10 ml of tetrahydrofuran, 3.9 ml of n-butyllithium (1.5 M, n-hexane solution) was added thereto at −70° C. under a nitrogen atmosphere, the mixture was stirred for 1 hour, and then a solution of 1 g of 1-benzylpiperidine-4-carboxaldehyde in tetrahydrofuran (5 ml) was added dropwise and the mixture was stirred for 1 hour. Water was added to the reaction solution, extraction was performed with ethyl acetate, the extract was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain 597 mg of (1-benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanol.

Aufarbeitung

additionwas added
stirringthe mixture was stirred for 1 hour
dry with materialthe extract was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customPurification

Quellen und Nachweise

ORD-Eintrag: ord-d445bdd01bee4deea3ae496410f0a6ed
Quelldatensatz: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07265108B2

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