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

HRID 514638Notes

Reaction equation

[O:1]([CH2:19][C:20]1([CH2:28][CH2:29][N:30]2[CH:34]=[CH:33][N:32]=[C:31]2[N+:35]([O-:37])=[O:36])[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:24][CH2:25][C:20]([CH2:19][OH:1])([CH2:28][CH2:29][N:30]2[CH:34]=[CH:33][N:32]=[C:31]2[N+:35]([O-:37])=[O:36])[CH2:21][O:22]1

Participants

Conditions

Temperature: 25 °C

Procedure

46 mg (0.088 mmol equivalents) of 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-1,3-dioxane was dissolved in 1 mL of tetrahydrofuran, 0.11 mL (1 mol/L solution, 0.11 mmol equivalents) of a solution of tetrabutylammonium fluoride in tetrahydrofuran was added thereto, and the mixture was stirred at room temperature (25° C.) for 1 hour. After completion of the reaction, the solvent was removed by distillation, and the obtained crude product was purified by silica gel column chromatography (eluent: chloroform/methanol (v/v)=10/1) to give 25 mg (0.086 mmol equivalents) of 2,2-dimethyl-5-hydroxymethyl-5-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-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: chloroform/methanol (v/v)=10/1)

Sources & evidence

ORD record: ord-f2a597fba8d04ebe907a15cfa7203bcc
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107964B2

Reaction notes

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