2-(6-{[(1R,2R)-2-(phenylmethoxy)cyclopentyl]amino}purin-9-yl)(4S,5S,3R)-5-(chloromethyl)oxolane-3,4-diol → 2-{6-[((1R,2R)-2-hydroxycyclopentyl)amino]-purin-9-yl}(4S,5S,3R)-5-(chloromethyl)oxolane-3,4-diol

HRID 1593930

Reaktionsgleichung

Reaktionsgleichung von HRID 1593930
C1(C[O:8][C@@H:9]2[CH2:13][CH2:12][CH2:11][C@H:10]2[NH:14][C:15]2[N:23]=[CH:22][N:21]=[C:20]3[C:16]=2[N:17]=[CH:18][N:19]3[CH:24]2[C@H:28]([OH:29])[C@H:27]([OH:30])[C@@H:26]([CH2:31][Cl:32])[O:25]2)C=CC=CC=1>C(O)C.C1CCCCC1.[OH-].[Pd+2].[OH-]>[OH:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[NH:14][C:15]1[N:23]=[CH:22][N:21]=[C:20]2[C:16]=1[N:17]=[CH:18][N:19]2[CH:24]1[C@H:28]([OH:29])[C@H:27]([OH:30])[C@@H:26]([CH2:31][Cl:32])[O:25]1

Komponenten

5

Edukt 1

HCID 671932342-(6-{[(1R,2R)-2-(phenylmethoxy)cyclopentyl]amino}purin-9-yl)(4S,5S,3R)-5-(chloromethyl)oxolane-3,4-diol

Produkt 1

HCID 671894862-{6-[((1R,2R)-2-hydroxycyclopentyl)amino]-purin-9-yl}(4S,5S,3R)-5-(chloromethyl)oxolane-3,4-diolAusbeute 41,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittelHCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

The 2-(6-{[(1R,2R)-2-(phenylmethoxy)cyclopentyl]amino}purin-9-yl)(4S,5S,3R)-5-(chloromethyl)oxolane-3,4-diol obtained in Example 3 (22 g) was dissolved in ethanol (450 mL) and cyclohexane (200 mL). To this solution was added palladium hydroxide (20 mole %, 1 gram added initially, 1 gram after 6 hours, and 1 gram after 14 hours), and the reaction mixture was refluxed for 18 hours. The reaction mixture was filtered thru celite while still hot, and solvent removed from the filtrate under reduced pressure. The product was triturated with ethanol (20 mL), filtered, and washed with ethanol, to afford 2-{6-[((1R,2R)-2-hydroxycyclopentyl)amino]purin-9-yl}(4S,5S,3R)-5-(chloromethyl)oxolane-3,4-diol as a white powder (7.3 grams).

Aufarbeitung

  1. additionadded initially
  2. temperature1 gram after 14 hours), and the reaction mixture was refluxed for 18 hours
  3. filtrationThe reaction mixture was filtered thru celite while still hot, and solvent
  4. customremoved from the filtrate under reduced pressure
  5. customThe product was triturated with ethanol (20 mL)
  6. filtrationfiltered
  7. washwashed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-cccad438d7f240678071374e0792adaf
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07300923B2

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