1-CYCLOPROPylpiPERIDINE-4-CARBOXYLIC ACID → [(3S,4R)-4-(4-chloro-phenyl)-1-(1-cyclopropyl-piperidine-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester

HRID 587380

Reaktionsgleichung

Reaktionsgleichung von HRID 587380
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:24])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15][NH:14][CH2:13]2)[CH3:11])=[CH:4][CH:3]=1.[CH:25]1([N:28]2[CH2:33][CH2:32][CH:31]([C:34](O)=[O:35])[CH2:30][CH2:29]2)[CH2:27][CH2:26]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:24])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15][N:14]([C:34]([CH:31]3[CH2:30][CH2:29][N:28]([CH:25]4[CH2:26][CH2:27]4)[CH2:33][CH2:32]3)=[O:35])[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 162440131-CYCLOPROPylpiPERIDINE-4-CARBOXYLIC ACIDHCID 67233751[(3S,4R)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester

Produkt 1

HCID 58303123[(3S,4R)-4-(4-chloro-phenyl)-1-(1-cyclopropyl-piperidine-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester

Versuchsvorschrift

In analogy to the procedure described for the synthesis of example 44 (step c), the title compound [(3S,4R)-4-(4-chloro-phenyl)-1-(1-cyclopropyl-piperidine-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester was prepared from [(3S,4R)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester instead of [(3S,4R)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester using 1-cyclopropyl-piperidine-4-carboxylic acid instead of 1-methylcyclopropane-1-carboxylic acid and was obtained as a white foam. MS m/e: 500.3 [M]+.

Aufarbeitung

  1. customIn analogy to the procedure described for the synthesis of example 44 (step c)
  2. customwas obtained as a white foam

Quellen und Nachweise

ORD-Eintrag
ord-58d133c29f2645b58bba991e0bb275a8
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09226916B2

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