Sodium Acetate → alpha-methylhistamine, (R)-

HRID 2380818Notes

Reaction equation

HRID 2380818 reaction equation
Br[CH2:2][C@@H:3]([NH2:10])[CH2:4][C:5]1[NH:6][CH:7]=[N:8][CH:9]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C.[Pd]>[N:8]1[CH:9]=[C:5]([CH2:4][C@H:3]([NH2:10])[CH3:2])[NH:6][CH:7]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 69071454(S)-1-bromomethyl-2-(3H-imidazol-4-yl)-ethylamine

Product 1

HCID 156615alpha-methylhistamine, (R)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1.5 g (S)-1-bromomethyl-2-(3H-imidazol-4-yl)-ethylamine and 1.87 g sodium acetate are dissolved in 94 mL acetic acid (10%). After the addition of 400 mg palladium/C the suspension is shaken under 3.5 bar H2 pressure at RT for about 60 h. After the catalyst has been filtered off the solvent is eliminated in vacuo and the crude product is used without further purification in the following reaction step.

Workup

  1. filtrationAfter the catalyst has been filtered off the solvent
  2. customthe crude product is used without further purification in the following reaction step

Sources & evidence

ORD record
ord-4e57b6a12239470298923adeef1c8ec0
Source dataset
uspto-grants-2012_09
Patent number
US08258129B2

Reaction notes

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