Di-tert-butyl azodicarboxylate → HCID 59504796, compound

HRID 873815Notes

Reaction equation

HRID 873815 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[N:6]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[N:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>C1COCC1>[CH:1]1([N:6]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 97268Di-tert-butyl azodicarboxylateHCID 178418630HCID 178418630, compound

Product 1

HCID 59504796HCID 59504796, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of cyclopropyl magnesium bromide in THF (104 mL, 52.1 mmol) under Ar was added di-tert-butyl azodicarboxylate (12 g, 52.1 mmol) in THF (50 mL) at −78° C. The reaction mixture was stirred for 30 min at this temperature, quenched with a saturated aq. NH4Cl solution, and extracted with EtOAc. The combined organic layers were washed with saturated aq. NH4Cl solution, dried over Na2SO4 and evaporated. The crude material was purified by silica gel column chromatography (hexane/EtOAc 2-10%) to afford the title product (11.84 g, 43.5 mmol, 83% yield) as a white solid. Rf=0.12 (CPS stain) (hexane/EtOAc 9:1)

Workup

  1. customquenched with a saturated aq. NH4Cl solution
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with saturated aq. NH4Cl solution
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe crude material was purified by silica gel column chromatography (hexane/EtOAc 2-10%)

Sources & evidence

ORD record
ord-6d5212e408434d8f8d99a89818ab6fa6
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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