HCID 86753081, compound → HCID 18979156, compound

HRID 2393170Notes

Reaction equation

HRID 2393170 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[N:20]O)[C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[CH3:2].NC(C1C=CC2C(=CC=CC=2)C=1)CCCCC(OCC)=O.[H][H]>C(O)(=O)C.[Pt]=O>[NH2:20][CH:9]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:22]

Participants

5

Reactant 2

HCID 86753081HCID 86753081, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18979156HCID 18979156, compoundYield 129.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

Ethyl 6-amino-6-(2-naphthyl)hexanoate Ethyl 6-hydroxyimino-6-(2-naphthyl)hexanoate (19.2 g) and platinum oxide (0.96 g) were suspended in acetic acid (160 ml) and the suspension was stirred in a hydrogen atmosphere at room temperature for 10 hours. The catalyst was then filtered off and the filtrate was concentrated. The residue was dispersed in saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. This extract was dried over anhydrous sodium sulfate and concentrated. The crude residue thus obtained was purified by silica gel column chromatography (ethyl acetate-methanol=10:1) to provide ethyl 6-amino-6-(2-naphthyl)hexanoate (12.1 g).

Workup

  1. filtrationThe catalyst was then filtered off
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was dispersed in saturated aqueous sodium hydrogen carbonate solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThis extract was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe crude residue thus obtained
  8. customwas purified by silica gel column chromatography (ethyl acetate-methanol=10:1)

Sources & evidence

ORD record
ord-24db851d4a1a41d89b9b2ef0e6c68be7
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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