Methyl cis(+/-)-4-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)pyridine-2-carboxylate → Methyl cis(+/-)-4-(4-amino-3-methoxypiperidin-1-yl)pyridine-2-carboxylate

HRID 43753

Reaction equation

HRID 43753 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]([O:26][CH3:27])=[O:25])[CH:19]=2)[CH2:14][C@H:13]1[O:28][CH3:29])=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[CH:23]=[CH:22][N:21]=[C:20]([C:24]([O:26][CH3:27])=[O:25])[CH:19]=2)[CH2:14][C@H:13]1[O:28][CH3:29]

Participants

5

Reactant 2

HCID 86648699Methyl cis(+/-)-4-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)pyridine-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86648700Methyl cis(+/-)-4-(4-amino-3-methoxypiperidin-1-yl)pyridine-2-carboxylateYield 42.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Methyl cis(±)-4-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)pyridine-2-carboxylate obtained in Example (160b) (74.8 mg) was dissolved in ethanol (10 mL). A 10% palladium-carbon catalyst (100 mg) was added, and the mixture was stirred in a hydrogen atmosphere overnight. The reaction solution was filtered through celite and then concentrated under reduced pressure, to obtain 21.2 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-76212657015f45a48ce3056a5a7b77bf
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Linked notes

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