Ammonium formate → {2-[3-((R)-2-Aminopropyl)phenyl]ethyl}carbamic Acid tert-Butyl Ester

HRID 2412295Notes

Reaction equation

HRID 2412295 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][C@H:17]([NH:19][C@@H](C2C=CC=CC=2)C)[CH3:18])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CCO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][C@H:17]([NH2:19])[CH3:18])[CH:11]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66781838(2-{3-[(R)-2-((R)-1-phenylethylamino)propyl]phenyl}ethyl)carbamic acid tert-butyl ester

Product 1

HCID 66782120{2-[3-((R)-2-Aminopropyl)phenyl]ethyl}carbamic Acid tert-Butyl Ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A stirred solution of (2-{3-[(R)-2-((R)-1-phenylethylamino)propyl]phenyl}ethyl)-carbamic acid tert-butyl ester (1.54 g, 4.02 mmol), palladium hydroxide on carbon (10 wt. %, ˜50% water, 2.24 g, 0.805 mmol), and ammonium formate (1.27 g, 20.1 mmol) in EtOH (50.0 mL) was heated gradually to 50° C. and then stirred at 50° C. for 1.5 h. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated under reduced pressure to give the title compound, which was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-88dba7251d9046f985d5851d647b43fa
Source dataset
uspto-grants-2014_08
Patent number
US08816088B2

Reaction notes

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