Di-tert-butyl azodicarboxylate → HCID 86648901, compound

HRID 384381Notes

Reaction equation

HRID 384381 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([CH3:12])([CH3:11])[CH2:5]2.C([Li])CCC.[N:18]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[N:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>O1CCCC1>[CH3:11][C:6]1([CH3:12])[CH:5]=[C:4]2[C:8]([CH:9]=[CH:10][C:2]([N:18]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[NH:19][C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])=[CH:3]2)=[CH:7]1

Participants

5

Reactant 3

HCID 97268Di-tert-butyl azodicarboxylateHCID 148388445-Bromo-2,2-dimethyl-2,3-dihydro-1H-indeneHCID 178418339Butyllithium

Product 1

HCID 86648901HCID 86648901, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

5-Bromo-2,2-dimethyl-indan 45b (2.4 g, 10.7 mmol) was dissolved in 20 mL of dry tetrahydrofuran. Upon cooling by a dry ice-ethanol bath to −78° C., n-butyllithium (12.1 mL, 30.2 mmol) was added dropwise. Upon completion of the addition, the mixture was stirred for 2 hours. A solution of di-tert-butyl azodicarboxylate (3.27 g, 14.2 mmol) in 20 mL of dry tetrahydrofuran was added to the above mixture. The reaction mixture was reacted at the same temperature for 3 hours. The reaction was monitored by TLC until the disappearance of the starting materials and quenched by addition of 50 mL of water. The mixture was extracted with ethyl acetate (50 mL×2). The combined organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound di-tert-butyl 1-(2,2-dimethyl-inden-5-yl)hydrazine-1,2-dicarboxylate 45c (2.68 g, yield 66.8%) as a yellow oil.

Workup

  1. additionUpon completion of the addition
  2. customThe reaction mixture was reacted at the same temperature for 3 hours
  3. customquenched by addition of 50 mL of water
  4. extractionThe mixture was extracted with ethyl acetate (50 mL×2)
  5. washThe combined organic extracts were washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customto remove the drying agent
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e9d6811914ab4772913aded9649275e0
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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