Ammonium formate → Methyl {3-[(2R)-2-aminopropyl]phenyl}acetate

HRID 494426Notes

Reaction equation

HRID 494426 reaction equation
C1([C@H]([NH:9][C@H:10]([CH3:23])[CH2:11][C:12]2[CH:13]=[C:14]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:15]=[CH:16][CH:17]=2)C)C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:9][C@H:10]([CH3:23])[CH2:11][C:12]1[CH:13]=[C:14]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 46938717methyl[3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate

Product 1

HCID 46938716Methyl {3-[(2R)-2-aminopropyl]phenyl}acetateYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of methyl [3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate (Preparation 89) (13.65 g, 40.9 mmol) and ammonium formate (12.9 g, 204 mmol) in ethanol (200 ml) was heated at reflux in the presence of 20% of palladium hydroxide on charcoal (Pd(OH)2/C, 1.36 g). After 3 hours the reaction mixture was cooled to room temperature, filtered through arbocel and the filtrate concentrated in vacuo. The residue was partitioned between dichloromethane (200 ml) and 880 ammonia (100 ml) and the organic phase separated. The aqueous phase was extracted with further dichlorormethane (3×100 ml) and the combined organic extracts washed with brine (100 ml), dried (sodium sulfate) and reduced in vacuo to give the title compound (8.48 g) as a pale yellow oil.

Workup

  1. filtrationfiltered through arbocel
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was partitioned between dichloromethane (200 ml) and 880 ammonia (100 ml)
  4. customthe organic phase separated
  5. extractionThe aqueous phase was extracted with further dichlorormethane (3×100 ml)
  6. washthe combined organic extracts washed with brine (100 ml)
  7. dry with materialdried (sodium sulfate)

Sources & evidence

ORD record
ord-3d72c30d1d2745df839609238fe97019
Source dataset
uspto-grants-2009_05
Patent number
US07538141B2

Reaction notes

Loading…