Di-tert-butyl azodicarboxylate → di-tert-butyl 1-(3,3-dimethyl-1H-inden-5-yl)hydrazine-1,2-dicarboxylate

HRID 384315Notes

Reaction equation

HRID 384315 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH3:12])[CH3:11])=[CH:4][CH:3]=1.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:8]1([CH3:12])[C:9]2[C:5](=[CH:4][CH:3]=[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:10]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 97268Di-tert-butyl azodicarboxylateHCID 124417856-bromo-1,1-dimethyl-2,3-dihydro-1H-indeneHCID 178418339Butyllithium

Product 1

HCID 59615676di-tert-butyl 1-(3,3-dimethyl-1H-inden-5-yl)hydrazine-1,2-dicarboxylateYield 37.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6-Bromo-1,1-dimethyl-indan (WO2005066115) 8g (4.32 g, 19.27 mmol) was dissolved in 40 mL of tetrahydrofuran and then butyllithium (15.67 mL, 1.6 mol/L, 25.05 mmol) was added dropwise at −78° C. After the reaction mixture was reacted for 40 minutes, a solution of di-tert-butyl azodicarboxylate (5.32 g, 23.12 mmol) in 30 mL of tetrahydrofuran was then added. The reaction mixture was reacted for another 3 hours at −78° C. The reaction was monitored by TLC until the disappearance of the starting materials and quenched with 5 mL of methanol. The mixture was warmed up to room temperature and filtered by silica gel. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound di-tert-butyl 1-(3,3-dimethyl-2,3-dihydro-1H-inden-5-yl)hydrazine-1,2-dicarboxylate 8h (2.70 g, yield 37.2%) as a yellow solid.

Workup

  1. customAfter the reaction mixture was reacted for 40 minutes
  2. customThe reaction mixture was reacted for another 3 hours at −78° C
  3. customquenched with 5 mL of methanol
  4. filtrationfiltered by silica gel
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0fb0c89f3c024fbaac74556d0491a9c4
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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