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 43811Notes

Reaction equation

HRID 43811 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-dc6a911f245a4c95b12b080cab82d2a7
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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