Reaktion #50345

Reaktionsgleichung

secondary amine

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

hydrochloric acid

sodium bicarbonate

→

title compound

(R)-2-[(Phenylisopropyl)Amino]Adenosine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheat
2. 2
   Sonstigethe reaction to 50° C. for 30 minutes
3. 3
   TemperaturCool
4. 4
   Sonstigethe reaction
5. 5
   ExtraktionExtract
6. 6
   Sonstigethe reaction with chloroform (3×150 ml)
7. 7
   TrocknenCombine the organic extracts, dry over anhydrous magnesium sulfate
8. 8
   Filtrationfilter
9. 9
   Einengenconcentrate under vacuum
10. 10
    SonstigePurify the residue by radial chromatography (2% to 4% to 8% to 15% methanol/chloroform, 4 mm plate) four times

Vorschrift

Treat the secondary amine (3) (249 mg, 0.57 mmol) with 1M hydrochloric acid (20 ml) and heat the reaction to 50° C. for 30 minutes. Cool the reaction and pour into saturated sodium bicarbonate (200 ml). Extract the reaction with chloroform (3×150 ml). Combine the organic extracts, dry over anhydrous magnesium sulfate, filter, and concentrate under vacuum. Purify the residue by radial chromatography (2% to 4% to 8% to 15% methanol/chloroform, 4 mm plate) four times to provide the title compound (105 mg) as the free base. Treat this with ethereal hydrogen chloride, filter, and dry the solid under high vacuum over phosphorous pentoxide to provide the hydrochloride salt of the Formula I (48 mg), m.p. 153° C. dec.; [α]D20 =30° (c=1.04, H2O)

Quelle