Ethyl oxoacetate → HCID 19699373, compound

HRID 863078

Reaction equation

HRID 863078 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([NH2:13])[CH2:7]2.[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[CH:15]=O>C(O)C.[Pd]>[CH2:19]([O:18][C:14](=[O:17])[CH2:15][NH:13][CH:6]1[CH2:5][CH2:4][C:3]2[C:8](=[CH:9][C:10]([F:12])=[CH:11][C:2]=2[F:1])[CH2:7]1)[CH3:20]

Participants

5

Reactant 2

HCID 70211Ethyl oxoacetateHCID 196994235,7-Difluoro-1,2,3,4-tetrahydronaphthalen-2-ylamine

Product 1

HCID 19699373HCID 19699373, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-ylamine (6.0 g, 32.8 mmol), prepared as in Example 8, and ethyl glyoxylate (4.6 g, 36.0 mmol) in 300 mL of ethanol was hydrogenated over 10% palladium on carbon (0.75 g) for 10 hours. The mixture was filtered and concentrated by evaporation. Purification of the residue by column chromatography on silica gel (elution: 30% ethyl acetate/hexane) gave ethyl[(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amino]acetate (7.5 g, 27.9 mmol) as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated by evaporation
  3. customPurification of the residue by column chromatography on silica gel (elution: 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-50e16a5b33bd4c9b8e2ac41645b2b19b
Source dataset
uspto-grants-1998_02
Patent number
US05719280

Linked notes

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