2',3'-Didehydro-2',3'-dideoxyadenosine → Dideoxyadenosine

HRID 2209754Notes

Reaction equation

HRID 2209754 reaction equation
[C@@H:1]1([N:8]2[C:17]3[N:16]=[CH:15][N:14]=[C:12]([NH2:13])[C:11]=3[N:10]=[CH:9]2)[O:7][C@H:4]([CH2:5][OH:6])[CH:3]=[CH:2]1>CO.[Pd]>[C@@H:1]1([N:8]2[C:17]3[N:16]=[CH:15][N:14]=[C:12]([NH2:13])[C:11]=3[N:10]=[CH:9]2)[O:7][C@H:4]([CH2:5][OH:6])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 649752',3'-Didehydro-2',3'-dideoxyadenosine

Product 1

HCID 20039DideoxyadenosineYield 44.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 7 (1.27 g) in methanol (325 ml) was hydrogenated at 15 psi in the presence of 10% Pd/C (0.65 g). The reaction mixture was filtered through celite and the filtrate was evaporated. Crystallization of the crude product from methanol gave 0.57 g of 10: mp 186°-188° C. (Lit. mp 185°-187° C.)

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe filtrate was evaporated
  3. customCrystallization of the crude product from methanol

Sources & evidence

ORD record
ord-51322fe2e220492a84bd0c12b2a13985
Source dataset
uspto-grants-1995_10
Patent number
US05455339

Reaction notes

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