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Diethyl Ether → (3R)-3-(2-Hydroxy-2,2-dithien-2-ylacetoxy)-1-methyl-1-(3-thien-2-ylpropyl)pyrrolidinium bromide

HRID 458884
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 458884
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][N:9]1[CH2:13][CH2:12][C@@H:11]([O:14][C:15](=[O:28])[C:16]([OH:27])([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)[C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)[CH2:10]1.C[Br:30].[CH3:31]COCC>C(#N)C.C(Cl)(Cl)Cl>[Br-:30].[OH:27][C:16]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)[C:15]([O:14][C@@H:11]1[CH2:12][CH2:13][N+:9]([CH3:31])([CH2:8][CH2:7][CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH2:10]1)=[O:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 6323Methyl BromideHCID 100485212-Hydroxy-2,2-dithien-2-ylacetic acid (3R)-1-(3-thien-2-ylpropyl)pyrrolidin-3-yl ester2×

Produkt 1

HCID 69479721(3R)-3-(2-Hydroxy-2,2-dithien-2-ylacetoxy)-1-methyl-1-(3-thien-2-ylpropyl)pyrrolidinium bromide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212
Chloroform
Lösungsmittel
HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

0.3 g (0.00069 mol) of 2-Hydroxy-2,2-dithien-2-ylacetic acid (3R)-1-(3-thien-2-ylpropyl)pyrrolidin-3-yl ester (Intermediate 1-3) were dissolved in 4 ml of acetonitrile and 6 ml of CHCl3. To this solution 3.45 ml (0.00345 mol) of a 1 M solution of methyl bromide in acetonitrile were added. After stirring the mixture at room temperature under N2 atmosphere during 24 h, the solvents were evaporated. Ether was added to the residue and the mixture stirred to obtain a solid. This solid was treated with ether several times, filtered and washed with ether. The yield was 0.34 g (93.2%) of the title compound as a mixture of two stereoisomers.

Aufarbeitung

  1. customthe solvents were evaporated
  2. additionEther was added to the residue
  3. stirringthe mixture stirred
  4. customto obtain a solid
  5. filtrationfiltered
  6. washwashed with ether
  7. additionThe yield was 0.34 g (93.2%) of the title compound as a mixture of two stereoisomers

Quellen und Nachweise

ORD-Eintrag
ord-14e2fe93548a4fa9af636063bc496cac
Quelldatensatz
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07192978B2

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