((R)-1-Phenylethyl)-(S)-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-ylamine → (S)-2,7,8,9-Tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-ylamine

HRID 25333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 25333
C1([C@H]([NH:9][C@@H:10]2[C:19]3[CH2:18][O:17][CH:16]=[CH:15][C:14]4=[CH:20][NH:21][CH:22]=[C:12]([C:13]=34)[CH2:11]2)C)C=CC=CC=1.[H][H]>O1CCCC1.[OH-].[Pd+2].[OH-]>[CH:22]1[NH:21][CH:20]=[C:14]2[CH:15]=[CH:16][O:17][CH2:18][C:19]3[C@@H:10]([NH2:9])[CH2:11][C:12]=1[C:13]2=3

Komponenten

5

Edukt 2

HCID 69738166((R)-1-Phenylethyl)-(S)-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-ylamineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 69738048(S)-2,7,8,9-Tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-ylamineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Compound (29) 609 mg was dissolved in tetrahydrofuran 20 ml. 20% Palladium(II)hydroxide 200 mg was added. A mixture was stirred in a hydrogen atomosphere for 22 h. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue obtained was chromatographed on aluminum oxide in chloroform to give the titled compound (31) as pale brown crystals, 337 mg. Yield 86%. Furthermore, this was recrystallized from methanol-isopropanol to give the titled compound (31) as pale brown crystals, m.p. 202-203° C.

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue obtained
  4. customwas chromatographed on aluminum oxide in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-bef4abc45ff44e46be142e66008f7e76
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858640B2

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