Nitronium tetrafluoroborate → HCID 66970452, compound

HRID 1361585Notes

Reaction equation

[O:1]=[N+:2]=[O:3].F[B-](F)(F)F.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH3:26])[CH2:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>C(#N)C>[C:9]([C:13]1[CH:14]=[CH:15][C:16]([N:19]([CH3:26])[CH2:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[C:17]([N+:2]([O-:3])=[O:1])[CH:18]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

Nitronium-tetrafluoroborate (2.14 g, 16.10 mmol) was dissolved in 40 mL aceonitrile, cooled to 0° C. and stirred for 15 min. A solution of N-(4-tert-Butyl-phenyl)-N,N′,N′-trimethyl-propane-1,3-diamine (Step 1, 2.0 g, 8.05 mmol) in 40 mL acetonitrile was added drop-wise over 10 min. The solution was stirred for 30 min at 0° C., warmed to RT, and stirred an additional 16 h. The reaction was extracted into EtOAc, washed twice with water, once with brine, dried over Mg2SO4, filtered, and concentrated in vacuo to yield a crude mixture that was purified by silica gel chromatography using a 10% MeOH/CH2Cl2 gradient to give the title compound as a brown oil. The correct regioisomer was determined to be the only product by H-NMR analysis. MS (M+H)+=294; Calc'd 293.40 for C16H27N3O2.

Workup

stirringThe solution was stirred for 30 min at 0° C.
temperaturewarmed to RT
stirringstirred an additional 16 h
extractionThe reaction was extracted into EtOAc
washwashed twice with water, once with brine
dry with materialdried over Mg2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customto yield a crude mixture that
customwas purified by silica gel chromatography

Sources & evidence

ORD record: ord-cb844becf5fa4852928c485858bc12d6
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880000B2

Reaction notes

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