Tert-Butyl nitrite → HCID 86607294, compound

HRID 552692Notes

Reaction equation

HRID 552692 reaction equation
[C:1]([O:4][C@H:5]1[CH2:9][C@H:8]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3N)[O:7][C@@H:6]1[CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])(=[O:3])[CH3:2].C[Si]([Br:33])(C)C.C(ON=O)(C)(C)C.C([O-])(O)=O.[Na+]>BrCBr.C(Cl)Cl>[C:1]([O:4][C@H:5]1[CH2:9][C@H:8]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[Br:33])[O:7][C@@H:6]1[CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 10906Tert-Butyl nitriteHCID 76113BromotrimethylsilaneHCID 516892Sodium BicarbonateHCID 67164566HCID 67164566, compound

Product 1

HCID 86607294HCID 86607294, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 3024DibromomethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-3-yl acetate (2.00 g, 4.91 mmol) in dibromomethane (98.2 mL) were added trimethylsilylbromide (0.717 mL, 5.55 mmol) then t-butylnitrite (3.98 mL, 33.44 mmol). The reaction mixture was stirred at room temperature for approximately 3 hours before being slowly poured into a 1:1 mixture of saturated NaHCO3:CH2Cl2. The organics were washed with water then brine. After drying over Na2SO4, the solvent was removed in vacuo. The crude product was purified by flash chromatography (0% to 30% EtOAc/Hex) to obtain the title compound as a yellow oil (1.26 g, 55%).

Workup

  1. washThe organics were washed with water
  2. dry with materialAfter drying over Na2SO4
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified by flash chromatography (0% to 30% EtOAc/Hex)

Sources & evidence

ORD record
ord-db681936b3394f3483aeb88d4f2c41e1
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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