Morpholine → Pyrrolidine, 2-(4-fluorophenyl)-1-[[4-(4-morpholinylmethyl)phenyl]sulfonyl]-, (2E)-2-butenedioate (1:1)

HRID 1594766

Reaktionsgleichung

Reaktionsgleichung von HRID 1594766
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22]Cl)=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[CH:4][CH:3]=1.FC1C=CC(C2CCCN2)=CC=1.BrCC1C=CC(S(Cl)(=O)=O)=CC=1.[NH:48]1[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1.[C:54]([O-:61])(=[O:60])/[CH:55]=[CH:56]/[C:57]([O-:59])=[O:58]>>[C:54]([OH:61])(=[O:60])/[CH:55]=[CH:56]/[C:57]([OH:59])=[O:58].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:48]3[CH2:53][CH2:52][O:51][CH2:50][CH2:49]3)=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[CH:4][CH:3]=1

Komponenten

6

Edukt 5

HCID 8083MorpholineHCID 27344094-(Bromomethyl)benzenesulfonyl chlorideHCID 38655602-(4-Fluorophenyl)pyrrolidineHCID 5460307FumarateHCID 21706775(RS)-2-(4-fluoro-phenyl)-1-(4-chloromethyl-benzenesulfonyl)-pyrrolidine

Produkt 1

HCID 69693329Pyrrolidine, 2-(4-fluorophenyl)-1-[[4-(4-morpholinylmethyl)phenyl]sulfonyl]-, (2E)-2-butenedioate (1:1)

Versuchsvorschrift

Reaction of (RS)-2-(4-fluoro-phenyl)-1-(4-chloromethyl-benzenesulfonyl)-pyrrolidine (0.50 g, 1.41 mmol), which was prepared in accordance with the general method of example 1e from (RS)-2-(4-fluoro-phenyl)-pyrrolidine and 4-bromomethyl-benzenesulfonyl chloride, with morpholine (K2CO3, DMF, 80° C., 17 h) and subsequent formation of the fumarate (MeOH, diethyl ether) yielded the title compound as an off-white solid, m.p. 136° C., and MS: m/e=405.4 (M+H+).

Quellen und Nachweise

ORD-Eintrag
ord-3cfff8c53bbb4df2b0a992a18537a59c
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06284785B1

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