Phenacyl bromide → (3R)-3-(2-(benzyloxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 1619513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619513
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:13]([O:15][C@@H:16]1[CH:21]2[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]2)[CH2:17]1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:30][CH2:31][C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:33]>CCOC(C)=O>[Br-:30].[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:13]([O:15][C@@H:16]1[CH:21]2[CH2:20][CH2:19][N+:18]([CH2:31][C:32](=[O:33])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([CH2:23][CH2:22]2)[CH2:17]1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 6259Phenacyl bromideHCID 67605836(R)-quinuclidin-3-yl 2-(benzyloxycarbonylamino)-2-phenylacetate

Produkt 1

HCID 86665824(3R)-3-(2-(benzyloxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromideAusbeute 85,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (R)-quinuclidin-3-yl 2-(benzyloxycarbonylamino)-2-phenylacetate (C29) (100 mg, 0.25 mmol) in EtOAc (5 ml), was added 2-bromo-1-phenylethanone (55.5 mg, 0.28 mmol), and the reaction was stirred at RT for 15 hours. The solvent was evaporated, and the resulting crude was purified by silica gel flash chromatography (DCM/MeOH=93/7) to obtain (3R)-3-(2-(benzyloxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (127.5 mg; 85% yield).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe resulting crude was purified by silica gel flash chromatography (DCM/MeOH=93/7)

Quellen und Nachweise

ORD-Eintrag
ord-832868ce819e42c5925cfede09345cf3
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772314B2

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