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

HRID 1866524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1866524
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-31b7c1f81eb84b57b7c97787ab6e615a
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629358B2

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