Reaktion #50346

ord-303a333fba484a8fbb5194a1b76974ce

Reaktionsgleichung

CC(C)(Nc1nc(N)c2ncn([C@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1)c1ccccc1
acetonide
CC(C)(Nc1nc(N)c2ncn([C@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1)c1ccccc1
(S)-2-[(phenylisopropyl)amino]adenosine
C[C@H](N)Cc1ccccc1
D-(+)-amphetamine
→
CCC(Nc1nc(N)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1)c1ccccc1
secondary amine
Ausbeute 74.8%
CCC(Nc1nc(N)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1)c1ccccc1
(R)-2-[(1-Phenylpropyl)amino]adenosine
Ausbeute 74.8%

Edukte

CC(C)(Nc1nc(N)c2ncn([C@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1)c1ccccc1
acetonide
CC(C)(Nc1nc(N)c2ncn([C@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1)c1ccccc1
(S)-2-[(phenylisopropyl)amino]adenosine
C[C@H](N)Cc1ccccc1
D-(+)-amphetamine

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturAfter cooling
  2. 2
    Sonstigepurify by flash chromatography (3% to 5% to 10% methanol/chloroform)

Vorschrift

Combine the acetonide (2) (638 mg, 1.87 mmol) with D-(+)-amphetamine (4.5 g) and heat to 130° C. for 5 hours under nitrogen with stirring. After cooling, purify by flash chromatography (3% to 5% to 10% methanol/chloroform) followed by radial chromatography four times (2% to 4% to 6% to 8% to 10% methanol/chloroform, 4 mm plate) to provide the secondary amine (3) (0.56 g).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05426101uspto-grants-1995_06