HCID 67364486, compound → HCID 67365815, compound

HRID 2174526Notes

Reaction equation

HRID 2174526 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[N:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3]1>C(O)C.[Pt].O>[CH3:1][C:2]1([CH3:19])[CH2:7][C:6]([CH3:8])([CH3:9])[CH2:5][CH:4]([NH:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3]1

Participants

5

Reactant 1

HCID 67364486HCID 67364486, compound

Product 1

HCID 67365815HCID 67365815, compoundYield 83.3%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

t-Butyl N′-(3,3,5,5-Tetramethylcyclohexylidene)hydrazine carboxylate (10.0 g, 0.0373 moles) was dissolved in ethanol (600 ml) and 5% Platinum on carbon (0.4 g) was added in water (2 mL). Stirred overnight under a hydrogen atmosphere (balloon). Filtered through HyFlo to remove the catalyst and evaporated the solvents to give a grey solid. Triturated with water and filtered off the grey solid. Dried in a desiccator to give the product as a grey solid (8.4 g, 83%). 1H NMR (300 MHz DMSO-d6) 8.1 (brm, 1H), 4.1 (brm, 1H), 2.95 (m, 1H), 1.45 (m, 2H), 1.35 (s, 9H), 1.15 (m, 1H), 0.95 (m, 1H), 0.95 (s, 6H), 0.9 (s, 6H).

Workup

  1. filtrationFiltered through HyFlo
  2. customto remove the catalyst
  3. customevaporated the solvents
  4. customto give a grey solid
  5. customTriturated with water
  6. filtrationfiltered off the grey solid
  7. customDried in a desiccator

Sources & evidence

ORD record
ord-c798e24fd39649f2be16965902467607
Source dataset
uspto-grants-2015_06
Patent number
US09062004B2

Reaction notes

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