Tert-Butyl nitrite → HCID 86607294, compound

HRID 552742Notes

Reaction equation

HRID 552742 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+]>C(Br)Br.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 CH2Br2 (98.2 mL) was added TMSBr (0.717 mL, 5.55 mmol) and t-butylnitrite (3.98 mL, 33.4 mmol). The reaction mixture was stirred at r.t. for 3 hours then slowly poured into 50 mL of a 1:1 mixture of saturated aq NaHCO3:CH2Cl2. The organic layer was washed with water (50 mL), brine (50 mL), dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 30% EtOAc/hexanes) to obtain the title compound as a yellow oil (1.26 g, 55%).

Workup

  1. washThe organic layer was washed with water (50 mL), brine (50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (0 to 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0e3c745772f54a61b84c258c2828f886
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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