rel-Methyl 2-[(3R,4S)-3-methoxy-4-[[(phenylmethoxy)carbonyl]amino]-1-piperidinyl]-1H-benzimidazole-7-carboxylate → Methyl cis(+/-)-2-(4-amino-3-methoxypiperidin-1-yl)-1H-benzimidazole-4-carboxylate

HRID 43811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 43811
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[NH:22][C:21]3[CH:23]=[CH:24][CH:25]=[C:26]([C:27]([O:29][CH3:30])=[O:28])[C:20]=3[N:19]=2)[CH2:14][C@H:13]1[O:31][CH3:32])=O)C1C=CC=CC=1.[H][H]>C(O)C.[C].[Pd]>[NH2:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[NH:22][C:21]3[CH:23]=[CH:24][CH:25]=[C:26]([C:27]([O:29][CH3:30])=[O:28])[C:20]=3[N:19]=2)[CH2:14][C@H:13]1[O:31][CH3:32]

Komponenten

5

Edukt 2

HCID 86648757rel-Methyl 2-[(3R,4S)-3-methoxy-4-[[(phenylmethoxy)carbonyl]amino]-1-piperidinyl]-1H-benzimidazole-7-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86648756Methyl cis(+/-)-2-(4-amino-3-methoxypiperidin-1-yl)-1H-benzimidazole-4-carboxylateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Methyl cis(±)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-1H-benzimidazole-4-carboxylate obtained in Example (187b) (330 mg) was dissolved in ethanol (15 mL). A 10% palladium-carbon catalyst (160 mg) was added, and the mixture was stirred in a hydrogen atmosphere throughout the day. The reaction solution was filtered through celite and then concentrated under reduced pressure to obtain 220 mg of the title compound as a colorless oily substance. The resulting compound was used for the next reaction without purification.

Aufarbeitung

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dc6a911f245a4c95b12b080cab82d2a7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

Notizen zur Reaktion

Wird geladen…