(2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxy-methyl)-5-[2-cyano-6-(cyclopentylamino)purin-9-yl]oxolan-3-yl acetate → (4S,2R,3R,5R)-2-[2-(aminomethyl)-6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

HRID 1724639Notes

Reaction equation

HRID 1724639 reaction equation
C([O:4][C@H:5]1[C@@H:9]([O:10]C(=O)C)[C@H:8]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([C:29]#[N:30])=[N:18][C:19]=3[NH:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[O:7][C@@H:6]1[CH2:31][O:32]C(=O)C)(=O)C>CO.[Ni]>[NH2:30][CH2:29][C:17]1[N:16]=[C:15]2[C:20]([N:21]=[CH:22][N:14]2[C@H:8]2[C@H:9]([OH:10])[C@H:5]([OH:4])[C@@H:6]([CH2:31][OH:32])[O:7]2)=[C:19]([NH:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:18]=1

Participants

4

Reactant 1

HCID 58767046(2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxy-methyl)-5-[2-cyano-6-(cyclopentylamino)purin-9-yl]oxolan-3-yl acetate

Product 1

HCID 57560745(4S,2R,3R,5R)-2-[2-(aminomethyl)-6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxy-methyl)-5-[2-cyano-6-(cyclopentylamino)purin-9-yl]oxolan-3-yl acetate (0.3 g) in methanol was added Raney nickel, and the mixture was stirred under hydrogen at 40 psi for 2 hours at room temperature. The catalyst was filtered off through celite, washed with methanol, and solvent removed from the filtrate under reduced pressure. The residue was crystallized from a mixture of methanol and hexane, to provide (4S,2R,3R,5R)-2-[2-(aminomethyl)-6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol. B. Preparation of a Compound of Formula (6) varying R1 and Y

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. washwashed with methanol, and solvent
  3. customremoved from the filtrate under reduced pressure
  4. customThe residue was crystallized from a mixture of methanol and hexane

Sources & evidence

ORD record
ord-59facb8a64a145febf914e0476470216
Source dataset
uspto-grants-2009_02
Patent number
US07488720B2

Reaction notes

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