HCID 59278467, compound → HCID 59278510, compound

HRID 1698241Notes

Reaction equation

HRID 1698241 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17](=[O:19])[NH2:18])[CH:12]=1)[CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2]>CO.C(O)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([CH:11]1[CH2:16][CH2:15][NH:14][CH:13]([C:17](=[O:19])[NH2:18])[CH2:12]1)[CH2:9][CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 1

HCID 59278467HCID 59278467, compound

Product 1

HCID 59278510HCID 59278510, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of [(S)-1-(2-carbamoyl-pyridin-4-yl)-propyl]-carbamic acid tert-butyl ester (1 g, 3.58 mmol) in MeOH (16.6 mL) and glacial acetic acid (3.3 mL) was added to a flask containing 10% palladium on carbon (0.38 g, 0.36 mmol) under nitrogen. The reaction was stirred at 60° C. under hydrogen at 400 psi using a Biotage Endeavour Argonaut instrument. After 20 hours, the reaction was filtered and concentrated. The crude material was diluted with EtOAc (100 mL), washed with saturated sodium carbonate solution (20 mL), brine, dried over sodium sulfate, filtered and concentrated to afford [(S)-1-(2-carbamoyl-piperidin-4-yl)-propyl]carbamic acid tert-butyl ester as a white solid.

Workup

  1. filtrationthe reaction was filtered
  2. concentrationconcentrated
  3. additionThe crude material was diluted with EtOAc (100 mL)
  4. washwashed with saturated sodium carbonate solution (20 mL), brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a7bd6f39e7c843b5927f7f3bae2b49af
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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