N'-(propan-2-ylidene)(tert-butoxy)carbohydrazide → N'-(propan-2-yl)(tert-butoxy)carbohydrazide

HRID 1816291Notes

Reaction equation

HRID 1816291 reaction equation
[CH3:1][C:2](=[N:4][NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH3:3]>[Pd].C(O)(=O)C>[CH:2]([NH:4][NH:5][C:6]([O:8][C:9]([CH3:11])([CH3:10])[CH3:12])=[O:7])([CH3:3])[CH3:1]

Participants

4

Reactant 1

HCID 11435207N'-(propan-2-ylidene)(tert-butoxy)carbohydrazide

Product 1

HCID 11217534N'-(propan-2-yl)(tert-butoxy)carbohydrazide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1-Methylethylidene-2-tert-butoxycarbonylhydrazine, glacial acetic acid (150 mL) and 10% palladium on carbon (2.0 g) were placed in a 500 mL Parr flask. The bottle was placed on a Parr apparatus, and after evacuating and flushing the bottle with nitrogen three times, the flask was charged with hydrogen to 40 psi. After hydrogen uptake ceased, the flask was evacuated and flushed with nitrogen. Filtration through celite, eluting with ethyl acetate, and concentration afforded the crude 1-(isopropyl)-2-tert-butoxycarbonylhydrazine as an acetic acid salt.

Workup

  1. customafter evacuating
  2. customflushing the bottle with nitrogen three times
  3. additionthe flask was charged with hydrogen to 40 psi
  4. customthe flask was evacuated
  5. customflushed with nitrogen
  6. filtrationFiltration through celite
  7. washeluting with ethyl acetate, and concentration

Sources & evidence

ORD record
ord-0849324a6ec6451f89c9d51f6e61325f
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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