rac-{(3S,4R)-4-(3,4-Dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-ethyl-carbamic acid 4-fluoro-phenyl ester → HCID 58312626, Verbindung

HRID 527503

Reaktionsgleichung

Reaktionsgleichung von HRID 527503
NC1C(C2C=CC(Cl)=C(Cl)C=2)CN(C(C2CCN(C(C3(C)CC3)=O)CC2)=O)C1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37](=[O:68])[N:38]([C@H:41]2[C@H:45]([C:46]3[CH:51]=[CH:50][C:49]([Cl:52])=[C:48](Cl)[CH:47]=3)[CH2:44][N:43](C(C3CCN(C(C4(C)CC4)=O)CC3)=O)[CH2:42]2)[CH2:39][CH3:40])=[CH:32][CH:31]=1>>[F:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37](=[O:68])[N:38]([C@H:41]2[C@H:45]([C:46]3[CH:47]=[CH:48][C:49]([Cl:52])=[CH:50][CH:51]=3)[CH2:44][NH:43][CH2:42]2)[CH2:39][CH3:40])=[CH:32][CH:31]=1

Komponenten

3

Edukt 2

HCID 53247231rac-{(3S,4R)-4-(3,4-Dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-ethyl-carbamic acid 4-fluoro-phenyl esterHCID 67238593HCID 67238593, Verbindung

Produkt 1

HCID 58312626HCID 58312626, Verbindung

Versuchsvorschrift

In analogy to the procedure described for rac-(3S,4R)-[3-Amino-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone (example 1, f) the Boc protecting group was removed. The liberated amine was reacted to the respective carbamate in analogy to the procedure described for the synthesis of rac-{(3S,4R)-4-(3,4-Dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-ethyl-carbamic acid 4-fluoro-phenyl ester (example 1, h). The benzyl protecting group was removed in analogy to the procedure described for rac-(3S,4R)-[4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (example 1, d) to yield the title compound as amorphous crude brown foam. MS m/e: 363.3 [M+H]+.

Aufarbeitung

  1. customwas removed
  2. customThe liberated amine was reacted to the respective carbamate in analogy to the procedure
  3. customThe benzyl protecting group was removed in analogy to the procedure

Quellen und Nachweise

ORD-Eintrag
ord-83463d2b3d5f4d74a69cb085676ab295
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346786B2

Verknüpfte Notizen

Wird geladen…