Ammonium formate → methyl 3-[(2S)-2-aminopropyl]benzoate

HRID 64456Notes

Reaction equation

HRID 64456 reaction equation
C1([C@@H]([NH:9][C@@H:10]([CH3:22])[CH2:11][C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=2)[C:15]([O:17][CH3:18])=[O:16])C)C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[C+4].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-]>[NH2:9][C@@H:10]([CH3:22])[CH2:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86713469methyl 3-[(2S)-2-{[(1S)-1-phenylethyl]amino}propyl]benzoate

Product 1

HCID 86713468methyl 3-[(2S)-2-aminopropyl]benzoateYield 98.9%

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 280 mg of methyl 3-[(2S)-2-{[(1S)-1-phenylethyl]amino}propyl]benzoate in 6.8 ml of ethanol were added 30 mg of 20% palladium-carbon hydroxide (wet) and 320 mg of ammonium formate, followed by stirring at 80° C. for 4 hours. The reaction mixture was filtered over Celite and the solvent was then evaporated under reduced pressure. To the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution and chloroform to carry out a layer separation operation, followed by drying over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 180 mg of methyl 3-[(2S)-2-aminopropyl]benzoate.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. customthe solvent was then evaporated under reduced pressure
  3. additionTo the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution and chloroform
  4. customa layer separation operation
  5. dry with materialby drying over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6aa1473429484d83946237626c3c6865
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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