Tetrahydrofuran → (3R)-3-{[(9-hydroxy-9H-fluoren-9-yl)carbonyl]oxy}-1-methyl-1-(4-oxo-4-phenylbutyl)pyrrolidinium formate

HRID 458886Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 458886
[CH3:1][N:2]1[CH2:6][CH2:5][C@@H:4]([O:7][C:8]([C:10]2([OH:23])[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)=[O:9])[CH2:3]1.ClC[CH2:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29].[CH2:36]1COCC1>>[CH:8]([O-:9])=[O:7].[OH:23][C:10]1([C:8]([O:7][C@@H:4]2[CH2:5][CH2:6][N+:2]([CH3:36])([CH2:1][CH2:26][CH2:27][C:28](=[O:29])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:3]2)=[O:9])[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2

Komponenten

4

Edukt 3

HCID 8028Tetrahydrofuran2×HCID 2535334-ChlorobutyrophenoneHCID 866022599-Hydroxy-9H-fluorene-9-carboxylic acid (3R)-1-methylpyrrolidin-3-yl ester

Produkt 1

HCID 69480233(3R)-3-{[(9-hydroxy-9H-fluoren-9-yl)carbonyl]oxy}-1-methyl-1-(4-oxo-4-phenylbutyl)pyrrolidinium formateAusbeute 7 %

Versuchsvorschrift

0.575 g (1.858 mmol) of 9-Hydroxy-9H-fluorene-9-carboxylic acid (3R)-1-methylpyrrolidin-3-yl ester (Intermediate I-10) and 1.018 g (5.576 mmol) of 4-chloro-1-phenylbutan-1-one in 6 ml of THF were refluxed for 20 days. After this time THF was poured off, and the residue was washed with THF in order to eliminate the alkylating agent. The product obtained (234 mg) was purified by preparative HPLC-MS to give 65 mg (7%) of the title compound (mixture of two stereoisomers) as a formate.

Aufarbeitung

  1. washthe residue was washed with THF in order
  2. customThe product obtained (234 mg)
  3. customwas purified by preparative HPLC-MS

Quellen und Nachweise

ORD-Eintrag
ord-242c962815b6439d85c4a09cc5133184
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192978B2

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