Dextroamphetamine → (R)-2-[(1-Phenylpropyl)amino]adenosine

HRID 22065

Reaktionsgleichung

Reaktionsgleichung von HRID 22065
[C:1]1([C:7]([NH:10][C:11]2[N:12]=[C:13]([NH2:29])[C:14]3[N:15]=[CH:16][N:17]([C:27]=3[N:28]=2)[C@H:18]2[O:26][C@H:23]([CH2:24][OH:25])[C@@H:21]([OH:22])[C@H:19]2[OH:20])([CH3:9])C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:30][C@H](N)CC1C=CC=CC=1.C1([C@H](N)CC)C=CC=CC=1.C1([C@@H](N)CC)C=CC=CC=1>>[C:1]1([CH:7]([NH:10][C:11]2[N:12]=[C:13]([NH2:29])[C:14]3[N:15]=[CH:16][N:17]([C:27]=3[N:28]=2)[C@@H:18]2[O:26][C@H:23]([CH2:24][OH:25])[C@@H:21]([OH:22])[C@H:19]2[OH:20])[CH2:9][CH3:30])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 4

HCID 5826DextroamphetamineHCID 5324978(R)-1-PhenylpropylamineHCID 6993773(1S)-1-phenylpropan-1-amineHCID 67681966(S)-2-[(phenylisopropyl)amino]adenosine

Produkt 1

HCID 53927112(R)-2-[(1-Phenylpropyl)amino]adenosine

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

In Scheme A, step b, the acetonide (2) is then treated with an appropriately substituted primary amine to provide the secondary amine of structure (3). More specifically, the acetonide (2) is combined with a large excess of an appropriately substituted primary amine, such as L-(-)-amphetamine, D-(+)-amphetamine, (R)-1-phenylpropylamine or (S)-1-phenylpropylamine, under an atmosphere of an inert gas such as nitrogen. The mixture is then heated to approximately 130° C. with stirring for approximately 3 to 6 hours. After cooling, the product can be isolated and purified by techniques well known to one skilled in the art. For example, the crude mixture can be directly purified by flash chromatography followed by radial chromatography using an appropriate eluent such as 3% to 6% methanol/chloroform to provide the secondary amine (3).

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe product can be isolated
  3. custompurified by techniques

Quellen und Nachweise

ORD-Eintrag
ord-91a42dcf5ab743dabf4e25dc19f9830e
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05426101

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