Reaktion #50348

Reaktionsgleichung

acetonide

(S)-2-[(phenylisopropyl)amino]adenosine

(R)-1-phenylpropylamine

→

secondary amine

Ausbeute 34.6%

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

Ausbeute 34.6%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux for 18 hours
2. 2
   SonstigeRemove some of the excess amine
3. 3
   workup.DISTILLATIONby distillation
4. 4
   TemperaturAfter cooling
5. 5
   Sonstigepurify by flash chromatography (3% methanol in dichloromethane)
6. 6
   SonstigeTriturate the product with diethyl ether

Vorschrift

Combine the acetonide (2) (3.4 g, 9.95 mmol) with (R)-1-phenylpropylamine (8.62 g) and heat to reflux for 18 hours. Remove some of the excess amine by distillation. After cooling, purify by flash chromatography (3% methanol in dichloromethane). Triturate the product with diethyl ether to provide the secondary amine (3) (1.38 g); 1H NMR (CDCl3) δ 7.41 (1H, s), 7.21-7.34 (4H, m), 7.14-7.22 (1H, m), 5.69 (1H, d), 5.50 (2H, s), 5.25 (1H, d), 5.10 (1H, t), 5.01 (1H, q), 4.90 (1H, q), 4.41 (1H, s), 3.93 (1H, d), 3.80 (1H, d), 1.82 (2H, pent), 1.60 (3H, s), 1.32 (3H, s), 0.94 (3H, t); IR (KBr) 3450-3100, 1633, 1599 cm-1. Anal. Calcd for C22H28N6O4 : C, 59.99; H, 6.41; N, 19.08. Found: C, 59.99; H, 6.38; N, 18.71.

Quelle