[2-(2-Ethyl-5-methyl-2H-pyrazol-3-yl)-ethyl]-carbamic acid benzyl ester → 2-(2-Ethyl-5-methyl-2H-pyrazol-3-yl)-ethylamine

HRID 1172585Notes

Reaction equation

HRID 1172585 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][C:13]1[N:14]([CH2:19][CH3:20])[N:15]=[C:16]([CH3:18])[CH:17]=1)C1C=CC=CC=1>CO.[Pd]>[CH2:19]([N:14]1[C:13]([CH2:12][CH2:11][NH2:10])=[CH:17][C:16]([CH3:18])=[N:15]1)[CH3:20]

Participants

4

Reactant 1

HCID 57659607[2-(2-Ethyl-5-methyl-2H-pyrazol-3-yl)-ethyl]-carbamic acid benzyl ester

Product 1

HCID 451214772-(2-Ethyl-5-methyl-2H-pyrazol-3-yl)-ethylamineYield 93.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

[2-(2-Ethyl-5-methyl-2H-pyrazol-3-yl)-ethyl]-carbamic acid benzyl ester (818 mg, 2.85 mmol) was dissolved in methanol (8 ml) and added to a suspension of Pd—C (10%, 163 mg) in methanol (8 ml), put under an atmosphere of hydrogen (1 bar) and stirring at rt was continued for 45 minutes. The reaction mixture was filtered over a pad of celite and the filtrate was concentrated under reduced pressure to give 408 mg (93.7%) of 2-(2-Ethyl-5-methyl-2H-pyrazol-3-yl)-ethylamine. LC-MS: tR=0.20 min, broad peak; [M+H]+=no ionization.

Workup

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

Sources & evidence

ORD record
ord-b479686c909c42a99535e1ec7e18087e
Source dataset
uspto-grants-2010_11
Patent number
US07834028B2

Reaction notes

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