Tetrabutylammonium Fluoride → 2,2-dimethyl-5-hydroxymethyl-5-[(4-methoxymethoxymethyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane

HRID 514628Notes

Reaction equation

[O:1]([CH2:19][C:20]1([CH2:28][N:29]2[CH:33]=[C:32]([CH2:34][O:35][CH2:36][O:37][CH3:38])[N:31]=[C:30]2[N+:39]([O-:41])=[O:40])[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22][CH2:21]1)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:26][C:23]1([CH3:27])[O:22][CH2:21][C:20]([CH2:19][OH:1])([CH2:28][N:29]2[CH:33]=[C:32]([CH2:34][O:35][CH2:36][O:37][CH3:38])[N:31]=[C:30]2[N+:39]([O-:41])=[O:40])[CH2:25][O:24]1

Participants

Conditions

Temperature: 25 °C

Procedure

86 mg (0.15 mmol equivalents) of 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(4-methoxymethoxymethyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane was dissolved in 1.0 mL of tetrahydrofuran, 0.17 mL (1 mol/L solution, 0.17 mmol equivalents) of a solution of tetrabutylammonium fluoride in tetrahydrofuran was added thereto, and the mixture was stirred at room temperature (25° C.) for 10 minutes. After completion of the reaction, the solvent was removed by distillation, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=1/1) to give 47 mg (0.14 mmol equivalents) of 2,2-dimethyl-5-hydroxymethyl-5-{(4-methoxymethoxymethyl-2-nitro-1H-imidazol-1-yl)methyl}-1,3-dioxane.

Workup

customAfter completion of the reaction
customthe solvent was removed by distillation
customthe obtained crude product
customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=1/1)

Sources & evidence

ORD record: ord-0e53594bb1654b22b587c2193d697700
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107964B2

Reaction notes

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