Imidazole → (1S,2R,4R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(6-chloro-9H-purin-9-yl)cyclopentanol

HRID 552734Notes

Reaction equation

HRID 552734 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[CH2:15][C@H:14]([OH:16])[C@@H:13]([CH2:17][OH:18])[CH2:12]1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].N1C=CN=C1>CN(C=O)C>[Si:19]([O:18][CH2:17][C@H:13]1[CH2:12][C@@H:11]([N:6]2[CH:5]=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[Cl:1])[CH2:15][C@@H:14]1[OH:16])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86607323(1S,2R,4R)-4-(6-chloro-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentanol

Product 1

HCID 86607322(1S,2R,4R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(6-chloro-9H-purin-9-yl)cyclopentanolYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1S,2R,4R)-4-(6-chloro-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentanol (0.496 g, 0.0018 mol) in DMF (10 mL) was added tert-butyldimethylsilyl chloride (0.348 g, 0.0023 mol), N,N-dimethylaminopyridine (0.023 g, 0.00019 mol) and imidazole (0.276 g, 0.0041 mol). This solution was stirred for 1 h and then the reaction mixture was quenched with water and diluted with ethyl acetate. The organic layer was washed with water, concentrated and purified by flash chromatography (0 to 50% EtOAc/DCM) to afford the title compound (0.462 g, 65%).

Workup

  1. customthe reaction mixture was quenched with water
  2. additiondiluted with ethyl acetate
  3. washThe organic layer was washed with water
  4. concentrationconcentrated
  5. custompurified by flash chromatography (0 to 50% EtOAc/DCM)

Sources & evidence

ORD record
ord-04815519d578443ba0437723d7fe71fc
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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