Ethanaminium, N,N,N-triethyl-, fluoride (1:1) → HCID 59201466, Verbindung

HRID 451715

Reaktionsgleichung

[Si]([O:8][CH2:9][CH2:10][O:11][C@:12]([C@@H:21]1[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]1)([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1)[CH3:13])(C(C)(C)C)(C)C.[F-].C([N+](CC)(CC)CC)C>CC#N>[Cl:20][C:16]1[CH:15]=[C:14]([C@@:12]([C@@H:21]2[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]2)([O:11][CH2:10][CH2:9][OH:8])[CH3:13])[CH:19]=[CH:18][CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

A mixture of (R)-tert-butyl 3-((R)-1-(2-(tert-butyldimethylsilyloxy)ethoxy)-1-(3-chlorophenyl)ethyl)piperidine-1-carboxylate, tetraethylammonium fluoride (7.600 g, 50.9 mmol) in CH3CN was heated at 45° C. for 1 h and then was allowed to stir at rt overnight. The reaction mixture was evaporated under reduced pressure, the residue was dissolved into water and extracted with Et2O (3×), dried over Na2SO4. After the solvent was removed in vacuo, the crude product was purified by reversed-phase HPLC to give 1.000 g (35% in two steps) of (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-hydroxyethoxy)ethyl)piperidine-1-carboxylate. MS ESI +ve m/z 406 (M+Na).

Aufarbeitung

customThe reaction mixture was evaporated under reduced pressure
dissolutionthe residue was dissolved into water
extractionextracted with Et2O (3×)
dry with materialdried over Na2SO4
customAfter the solvent was removed in vacuo
customthe crude product was purified by reversed-phase HPLC

Quellen und Nachweise

ORD-Eintrag: ord-848e0f9c20c841f79ce5223618f2da14
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08487108B2

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