Diisobutylaluminumhydride → HCID 66705597, compound

HRID 1881419Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([C:21]2[N:22]([S:32]([N:35]([CH3:37])[CH3:36])(=[O:34])=[O:33])[CH:23]=[C:24]([CH2:26][C:27]([CH3:31])([CH3:30])[CH2:28][CH3:29])[N:25]=2)=[O:20])=[CH:14][CH:13]=1>C(Cl)Cl>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([C:21]2[N:22]([S:32]([N:35]([CH3:37])[CH3:36])(=[O:33])=[O:34])[CH:23]=[C:24]([CH2:26][C:27]([CH3:31])([CH3:30])[CH2:28][CH3:29])[N:25]=2)[OH:20])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Diisobutylaluminum hydride (1 M in methylene chloride) (31 mL, 31 mmol) was added to a −78° C. solution of 2-[(4-bromophenyl)acetyl]-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (intermediate 8) (7.03 g, 15.5 mmol) in methylene chloride (100 mL). After stirring at −78° C. for 1 h, the reaction mixture was quenched with saturated aqueous sodium potassium tartrate and stirred vigorously at ambient temperature until layers separated. The aqueous phase was extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% ethyl acetate/hexane afforded 2-[2-(4-bromophenyl)-1-hydroxyethyl]-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Workup

customthe reaction mixture was quenched with saturated aqueous sodium potassium tartrate
stirringstirred vigorously at ambient temperature until layers
customseparated
extractionThe aqueous phase was extracted with methylene chloride
dry with materialThe combined organic extracts were dried (magnesium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-47988002a0484112a308fe1e91654e32
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318767B2

Reaction notes

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