N1,5'-O-dibenzyl-2',3'-didehydro-2',3'-dideoxyinosine → N1,5'-O-dibenzyl-2',3'-dideoxyinosine

HRID 889574Notes

Reaction equation

HRID 889574 reaction equation
[CH2:1]([N:8]1[CH:30]=[N:29][C:28]2[N:13]([C@@H:14]3[O:27][C@H:17]([CH2:18][O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:16]=[CH:15]3)[CH:12]=[N:11][C:10]=2[C:9]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[C].[Pd].CO>[CH2:1]([N:8]1[CH:30]=[N:29][C:28]2[N:13]([C@@H:14]3[O:27][C@H:17]([CH2:18][O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:16][CH2:15]3)[CH:12]=[N:11][C:10]=2[C:9]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11683075N1,5'-O-dibenzyl-2',3'-didehydro-2',3'-dideoxyinosineHCID 178418361HCID 178418361, compound

Product 1

HCID 11647353N1,5'-O-dibenzyl-2',3'-dideoxyinosineYield 90%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a methanol solution (1 mL) of N1,5′-O-dibenzyl-2′,3′-didehydro-2′,3′-dideoxyinosine (207 mg, 0.5 mmol), 5% palladium-carbon (20 mg) was added, and the mixture was stirred at room temperature for 2 hours in an atmosphere of hydrogen (1 atm). The palladium catalyst was removed from the obtained reaction mixture by filtration, and the resultant filtrate was concentrated under reduced pressure. After purification by chromatography (using 15 g of silica gel and ethyl acetate as an eluting solution), 187 mg of the intended product was obtained in a yield of 90% as a white solid.

Workup

  1. customThe palladium catalyst was removed from the obtained reaction mixture by filtration
  2. concentrationthe resultant filtrate was concentrated under reduced pressure
  3. customAfter purification by chromatography (
  4. customwas obtained in a yield of 90% as a white solid

Sources & evidence

ORD record
ord-0b6a2586d998423c9507f8712130dcc1
Source dataset
uspto-grants-2012_08
Patent number
US08252920B2

Reaction notes

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