Pyridine → (1S,2R,4R)-4-(6-chloro-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentanol

HRID 552733Notes

Reaction equation

HRID 552733 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[CH2:33][C@@H:14]2[O:15][Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)[O:19][CH2:20][C@H:13]2[CH2:12]1.F.N1C=CC=CC=1>C1COCC1.N1C=CC=CC=1>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[CH2:33][C@H:14]([OH:15])[C@@H:13]([CH2:20][OH:19])[CH2:12]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 14917Hydrofluoric AcidHCID 866073206-chloro-9-[(6aR,8R,9aS)-2,2,4,4-tetraisopropylhexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-8-yl]-9H-purine

Product 1

HCID 86607323(1S,2R,4R)-4-(6-chloro-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentanolYield 63.6%

Reagents, catalysts & solvents 1

HCID 16069498Pyridine tetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-9-[(6aR,8R,9aS)-2,2,4,4-tetraisopropylhexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-8-yl]-9H-purine (0.518 g, 1.0 mmol) in THF/pyridine (5.2 mL, 1:1) was added hydrofluoric acid in pyridine (0.381 mL, 15.2 mmol). The reaction was stirred for 14 h then quenched with saturated aq NaHCO3 and concentrated under reduced pressure. The residue was dissolved in 10% solution of MeOH/DCM, filtered, the organic layer was concentrated and the residue purified by flash chromatography (0 to 10% MeOH/DCM to afford the title compound (0.171 g, 63%).

Workup

  1. customthen quenched with saturated aq NaHCO3
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 10% solution of MeOH/DCM
  4. filtrationfiltered
  5. concentrationthe organic layer was concentrated
  6. customthe residue purified by flash chromatography (0 to 10% MeOH/DCM

Sources & evidence

ORD record
ord-e1e08518b9084e72bfa8404ea953dffd
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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