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

HRID 1866524Notes

Reaction equation

HRID 1866524 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][C@H:12]([NH:14][C@@H](C2C=CC=CC=2)C)[CH3:13])[CH:6]=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:14][C@H:12]([CH3:13])[CH2:11][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:23])[CH:10]=[CH:9][CH:8]=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 64) (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. 1H NMR (400 MHz, CDCl3): δ=7.90-7.87 (2H, m), 7.38-7.34 (2H, m), 3.90 (3H, s), 3.26-3.17 (1H, m), 2.78-2.73 (1H, dd), 2.64-2.59 (1H, dd), 1.14-1.12 (3H, d) ppm. LRMS (electrospray): m/z [M+H]+ 194.

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-31b7c1f81eb84b57b7c97787ab6e615a
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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