2-Bromo-2'-acetonaphthone → (R)-1-(2-(naphthalen-2-yl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide

HRID 453691

Reaktionsgleichung

[C:1]1([C@@H:7]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:26][CH2:27][C:28]([C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=1)=[O:29]>C(#N)C>[Br-:26].[CH:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:38]=[CH:39][C:30]=1[C:28](=[O:29])[CH2:27][N+:13]12[CH2:14][CH2:15][CH:16]([CH2:17][CH2:18]1)[C@@H:11]([O:10][C:8](=[O:9])[C@@H:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12]2

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (diastereomer 1 of I2) (75 mg, 0.22 mmol) in acetonitrile (5 ml), was added 2-bromo-1-(naphthalen-2-yl)ethanone (55.5 mg, 0.22 mmol) and the reaction was stirred at 100° C. for 70 minutes under microwave irradiation (UPLC-MS: complete conversion). The solvent was evaporated and the crude was triturated with i-Pr2O-EtOAc (9/1) to obtain (R)-1-(2-(naphthalen-2-yl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (121.9 mg, 93% yield).

Aufarbeitung

customThe solvent was evaporated
customthe crude was triturated with i-Pr2O-EtOAc (9/1)

Quellen und Nachweise

ORD-Eintrag: ord-76c6a67004fc4d24ac3ab0742093a29d
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08492548B2

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