Dichloromethane → (R)-2-(4-methoxybenzoylamino)-2-phenylethylamine

HRID 23954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 23954
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7]([NH:9][C@H:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][N:12]=[N+]=[N-])=[O:8])=[CH:5][CH:4]=1.C(Cl)Cl.C(OCC)(=O)C>[Pd].C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7]([NH:9][C@H:10]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:11][NH2:12])=[O:8])=[CH:5][CH:4]=1

Komponenten

7

Edukt 3

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 53998160(R)-2-(4-Methoxybenzoylamino)-2-phenylethylazide

Produkt 1

HCID 54421380(R)-2-(4-methoxybenzoylamino)-2-phenylethylamineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(R)-2-(4-methoxybenzoylamino)-2-phenylethyl azide (46.3 g) was combined with 10% palladium on carbon in THF (400 mL), methanol (100 mL) and was stirred under a hydrogen atmosphere. Analysis by TLC (70% methylene chloride, ethyl acetate) indicated absence of starting material after stirring overnight. The solution was filtered through diatomaceous earth, rinsed with THF, and evaporated. The resulting solid was recrystallized with ethyl acetate, and dried under vacuum at 60° C. for 1 h to afford 35.4 g (84%) of a white crystalline solid.

Aufarbeitung

  1. stirringafter stirring overnight
  2. filtrationThe solution was filtered through diatomaceous earth
  3. washrinsed with THF
  4. customevaporated
  5. customThe resulting solid was recrystallized with ethyl acetate
  6. customdried under vacuum at 60° C. for 1 h

Quellen und Nachweise

ORD-Eintrag
ord-f617e1f8d1bf48c58b8ab056d9ae01f2
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855715B1

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