HCID 12928224, compound → HCID 12928225, compound

HRID 1703353Notes

Reaction equation

HRID 1703353 reaction equation
[N:1]([CH:4]([CH2:10][CH:11]([F:16])[C:12]([F:15])([F:14])[Cl:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-].[H][H]>C(O)C.[Pd]>[NH2:1][CH:4]([CH2:10][CH:11]([F:16])[C:12]([F:14])([F:15])[Cl:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 12928224HCID 12928224, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12928225HCID 12928225, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Thereafter, 4.76 g (0.018 mol) of ethyl 2-azido-4,5,5-trifluoro-5-chloropentanoate was dissolved in 20 ml of ethanol. The resultant solution was placed in a three-neck round-bottom flask and 0.50 g of 5% palladium-containing activated carbon was added to the solution, and hydrogen was passed through the resultant mixture at a flow rate of 20 ml/min at room temperature for 22 hours. The catalyst was separated by filtration and the ethanol was expelled by distillation. By vacuum distilling the residual liquid, there was obtained 293 g (0.013 mol, yield of 69%) of ethyl 2-amino-4,5,5-trifluoro-5-chloropentanoate having b.p. 69° to 70° C./3 mm, nD20 1.4102, νNH2 3386 and 3318 cm-1 and νC=O 1733 cm-1.

Workup

  1. customThe catalyst was separated by filtration
  2. distillationthe ethanol was expelled by distillation
  3. distillationBy vacuum distilling the residual liquid

Sources & evidence

ORD record
ord-8b234b4c212841a8b0ab5cf0661633d6
Source dataset
uspto-grants-1982_09
Patent number
US04351954

Reaction notes

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