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

HRID 22070

Reaktionsgleichung

Reaktionsgleichung von HRID 22070
[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.[C:30]1([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

3

Edukt 2

HCID 5324978(R)-1-PhenylpropylamineHCID 67681966(S)-2-[(phenylisopropyl)amino]adenosine

Produkt 1

HCID 53927112(R)-2-[(1-Phenylpropyl)amino]adenosineAusbeute 34,6 %

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureto reflux for 18 hours
  2. customRemove some of the excess amine
  3. distillationby distillation
  4. temperatureAfter cooling
  5. custompurify by flash chromatography (3% methanol in dichloromethane)
  6. customTriturate the product with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-6e1e230f243a4e8fb0d1986d72dd21b0
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05426101

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