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

HRID 916070Notes

Reaction equation

HRID 916070 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][C@H:13]([NH:15][C@@H](C2C=CC=CC=2)C)[CH3:14])[CH:7]=1.C([O-])=O.[NH4+]>>[CH3:2][O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][C@H:13]([NH2:15])[CH3:14])[CH:7]=1

Participants

3

Reactant 2

HCID 2723923Ammonium formateHCID 46938908methyl[3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate hydrochloride

Product 1

HCID 46938716Methyl {3-[(2R)-2-aminopropyl]phenyl}acetateYield 104.8%

Procedure

A solution of methyl-[3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate hydrochloride (Preparation 42) (7.69 g, 22.0 mmol) and ammonium formate (6.94 g, 110 mmol) was heated to 75° C. in the presence of 20% palladium hydroxide-on-charcoal (Pd(OH)2/C, 2.00 g). After 90 minutes the reaction mixture was cooled to room temperature, filtered through arbocel and the filtrate concentrated in vacuo. The residue was partitioned between dichloromethane (100 ml) and 880 ammonia (100 ml) and the organic phase separated. The aqueous phase was extracted dichloromethane (100 ml) and the combined organic extracts dried (magnesium sulfate) and reduced in vacuo to give the title compound as a colourless oil (4.78 g).

Workup

  1. filtrationfiltered through arbocel
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was partitioned between dichloromethane (100 ml) and 880 ammonia (100 ml)
  4. customthe organic phase separated
  5. extractionThe aqueous phase was extracted dichloromethane (100 ml)
  6. dry with materialthe combined organic extracts dried (magnesium sulfate)

Sources & evidence

ORD record
ord-0648e9ae8db848c48f9bc09a5e06432b
Source dataset
uspto-grants-2007_09
Patent number
US07268147B2

Reaction notes

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