Acetic Acid → HCID 86704450, compound

HRID 1754395Notes

Reaction equation

HRID 1754395 reaction equation
[CH3:1][C:2]1([CH3:12])[N:10]2[CH:5]([CH2:6][CH:7]=[CH:8][C:9]2=[O:11])[CH2:4][CH2:3]1.[N:13]([Si](C)(C)C)=[N+:14]=[N-:15].CC(O)=O.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[N:13]([C:7]1[CH:6]=[C:5]2[N:10]([C:2]([CH3:12])([CH3:1])[CH2:3][CH2:4]2)[C:9](=[O:11])[CH:8]=1)=[N+:14]=[N-:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 78378AzidotrimethylsilaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86704451HCID 86704451, compound

Product 1

HCID 86704450HCID 86704450, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,3,8,8a-tetrahydro-3,3-dimethylindolizin-5(1H)-one (0.3 g, 1.8 mmol) in 10 ml of toluene was taken a 25 ml RB flask. To the above flask azido-trimethylsilane (2.42 ml, 18.2 mmol), AcOH (1.2 ml, 20 mmol) and DBU (0.27 ml, 1.8 mmol) were added. The reaction mixture was stirred at room temperature for overnight. Volatiles were removed under vacuum and the crude reaction mixture was purified by column chromatography. The product was obtained as colorless oil in 85% yield (0.32 g).

Workup

  1. customVolatiles were removed under vacuum
  2. customthe crude reaction mixture
  3. customwas purified by column chromatography
  4. customThe product was obtained as colorless oil in 85% yield (0.32 g)

Sources & evidence

ORD record
ord-643b46786fe14a3ca562d34fc2de7b84
Source dataset
uspto-grants-2015_10
Patent number
US09169249B2

Reaction notes

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