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

HRID 494423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494423
Cl.C1([C@H]([NH:10][C@H:11]([CH3:24])[CH2:12][C:13]2[CH:14]=[C:15]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:16]=[CH:17][CH:18]=2)C)C=CC=CC=1.C([O-])=O.[NH4+]>>[NH2:10][C@H:11]([CH3:24])[CH2:12][C:13]1[CH:14]=[C:15]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:16]=[CH:17][CH:18]=1

Komponenten

3

Edukt 2

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

Produkt 1

HCID 46938716Methyl {3-[(2R)-2-aminopropyl]phenyl}acetateAusbeute 104,8 %

Versuchsvorschrift

A solution of methyl [3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate hydrochloride (Preparation 23) (7.69 g, 22 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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-5dd8b7b88c0b4862aab3642c75eaf367
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538141B2

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