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

HRID 514613Notes

Reaction equation

HRID 514613 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>>[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

3

Reactant 2

HCID 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-dioxane

Procedure

Subsequently, the obtained 5-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane is reacted with tetra-n-butylammonium fluoride in an organic solvent by for example a method of E. J. Corey et al. (Journal of American Chemical Society, 1972, 94, p. 6190) and purified, to give 2,2-dimethyl-5-hydroxymethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane (FIG. 1, Step 4).

Workup

  1. customCorey et al. (Journal of American Chemical Society, 1972, 94, p. 6190) and purified

Sources & evidence

ORD record
ord-031aec7912944f83ac8756427ec63d28
Source dataset
uspto-grants-2015_08
Patent number
US09107964B2

Reaction notes

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