Tert-Butyl nitrite → HCID 86607300, compound

HRID 552699Notes

Reaction equation

HRID 552699 reaction equation
[C:1]([O:4][C@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[O:7][C@H:6]1[N:26]1[CH:34]=[N:33][C:32]2[C:27]1=[N:28][CH:29]=[N:30][C:31]=2N)(=[O:3])[CH3:2].C[Si]([Br:40])(C)C.C(ON=O)(C)(C)C.C(=O)(O)[O-].[Na+]>BrCBr.ClCCl>[C:1]([O:4][C@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[O:7][C@H:6]1[N:26]1[CH:34]=[N:33][C:32]2[C:27]1=[N:28][CH:29]=[N:30][C:31]=2[Br:40])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 10906Tert-Butyl nitriteHCID 76113BromotrimethylsilaneHCID 516892Sodium BicarbonateHCID 86607301HCID 86607301, compound

Product 1

HCID 86607300HCID 86607300, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 3024DibromomethaneSolventHCID 6344DichloromethaneSolvent

Procedure

(2R,3S,4R,5R)-2-(6Amino-9H-purin-9-yl)-5-{[(triisopropylsilyl)oxy]methyl}-tetrahydrofuran-3,4-diyl diacetate (0.605 g, 1.19 mmol) was dissolved in dibromomethane (24 mL). Trimethylsilyl bromide (0.17 mL, 1.35 mmol) was added dropwise followed by tert-butylnitrite (0.97 mL, 8.12 mmol). The orange solution was stirred for 2.5 hours then slowly poured into a 1:1 mixture of saturated sodium bicarbonate and dichloromethane and extracted. The pale yellow organic layer was washed with water and brine, dried (Na2SO4), filtered and concentrated. The yellow solid was purified by flash chromatography eluting with 25% ethyl acetate/hexanes to give the title compound as a yellow solid (0.402 g, 52%).

Workup

  1. extractionextracted
  2. washThe pale yellow organic layer was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe yellow solid was purified by flash chromatography
  7. washeluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0b4d8aeacfb9441d9050eef99447eaac
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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