Water → 2,2-dimethyl-5-hydroxymethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane

HRID 514618Notes

Reaction equation

HRID 514618 reaction equation
[O:1]([CH2:9][C:10]1([CH2:18][N:19]2[CH:23]=[CH:22][N:21]=[C:20]2[N+:24]([O-:26])=[O:25])[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12][CH2:11]1)[Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+].O>O1CCCC1>[CH3:16][C:13]1([CH3:17])[O:12][CH2:11][C:10]([CH2:9][OH:1])([CH2:18][N:19]2[CH:23]=[CH:22][N:21]=[C:20]2[N+:24]([O-:26])=[O:25])[CH2:15][O:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 903005825-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane

Product 1

HCID 894723022,2-dimethyl-5-hydroxymethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxaneYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

363 mg (0.942 mmol equivalents) of 5-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane was dissolved in 10.0 mL of tetrahydrofuran, 0.94 mL (1.0 mol/L solution, 0.94 mmol equivalents) of a tetrahydrofuran solution of tetrabutylammonium fluoride was added thereto, and the mixture was stirred at room temperature (25° C.) for 10 minutes. After completion of the reaction, a saturated aqueous solution of ammonium chloride and water were added thereto, and the mixture was extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water and brine, then dried with anhydrous magnesium sulfate and subsequently concentrated under vacuum, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=1/3) to give 221 mg (0.815 mmol equivalents) of 2,2-dimethyl-5-hydroxymethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane.

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. washThe combined ethyl acetate layers were washed with water and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationsubsequently concentrated under vacuum
  6. customthe obtained crude product
  7. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=1/3)

Sources & evidence

ORD record
ord-986072ca47c54ca393eb91403a601040
Source dataset
uspto-grants-2015_08
Patent number
US09107964B2

Reaction notes

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