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 1425275Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1425275
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-1c80ce3fce10468ca60c74f14aea1eea
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927588B2

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