Ammonium formate → methyl 4'-[2-[[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]-amino]ethyl]-1,1'-biphenyl-4-carboxylate

HRID 1823128Notes

Reaction equation

HRID 1823128 reaction equation
C([N:8]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([O:35][CH3:36])=[O:34])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[CH2:9][C@@H:10]([C:12]1[CH:13]=[N:14][C:15](Cl)=[CH:16][CH:17]=1)[OH:11])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO.O>[OH:11][C@H:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH2:9][NH:8][CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([O:35][CH3:36])=[O:34])=[CH:29][CH:28]=2)=[CH:25][CH:26]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 86590696methyl 4'-[2-[N-benzyl-N-[(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl]amino]ethyl]-1,1'-biphenyl-4-carboxylate

Product 1

HCID 69051982methyl 4'-[2-[[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]-amino]ethyl]-1,1'-biphenyl-4-carboxylateYield 92.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 4′-[2-[N-benzyl-N-[(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl]amino]ethyl]-1,1′-biphenyl-4-carboxylate (470 mg), ammonium formate (296 mg) and palladium on carbon powder (100 mg) in methanol (10 ml) and water (1.0 ml) was refluxed for 30 minutes. The reaction mixture was filtrated and poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. A mixture of the residue was chromatographed (chloroform-methanol) over silica gel to give methyl 4′-[2-[[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]-amino]ethyl]-1,1′-biphenyl-4-carboxylate (326 mg) as a colorless foam.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. additionpoured into water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. additionA mixture of the residue
  8. customwas chromatographed (chloroform-methanol) over silica gel

Sources & evidence

ORD record
ord-66f8b8e0129a4557acf0daf67d131c23
Source dataset
uspto-grants-2006_05
Patent number
US07037938B2

Reaction notes

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