(R)-1-(2-azido-propyl)-4,5-dihydro-8-methoxy-1H-benz[g]indole → (R)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethylamine

HRID 264456Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 264456
[N:1]([C@H:4]([CH3:21])[CH2:5][N:6]1[C:14]2[C:13]3[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:12]=3[CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7]1)=[N+]=[N-]>C(O)C.[Pt]=O>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:12]2[CH2:11][CH2:10][C:9]3[CH:8]=[CH:7][N:6]([CH2:5][C@H:4]([NH2:1])[CH3:21])[C:14]=3[C:13]=2[CH:15]=1

Komponenten

4

Edukt 1

HCID 54279251(R)-1-(2-azido-propyl)-4,5-dihydro-8-methoxy-1H-benz[g]indole

Produkt 1

HCID 22874712(R)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethylamineAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

1.9 g of (R)-1-(2-azido-propyl)-4,5-dihydro-8-methoxy-1H-benz[g]indole dissolved in 100 ml of anhydrous ethanol were hydrogenated on 190 mg of platinum oxide for 16 hours. The catalyst was subsequently filtered off, rinsed with ethonal and the solvent was drawn off in a vacuum. There were obtained 1.64 g (95%) of (R)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethylamine as a colorless oil, of which 440 mg were dissolved in 70 ml of anhydrous ether, filtered and treated while stirring with a solution of 200 mg of fumaric acid in 20 ml of methanol the mixture was stirred at room temperature for 2 hours and the white crystals were subsequently filtered off. 450 mg (70%) of (R)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethylamine fumarate (1:1) with m.p. 194° were obtained.

Aufarbeitung

  1. filtrationThe catalyst was subsequently filtered off
  2. washrinsed with ethonal and the solvent

Quellen und Nachweise

ORD-Eintrag
ord-ef92a5c58f3b480c99caaecf0b933365
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646173

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