5-Isopentyl-3-methylisoxazole → 2-Amino-7-methyloct-2-en-4-one

HRID 557405Notes

Reaction equation

HRID 557405 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[O:4][N:3]=1.[H][H]>[Pt](=O)=O.C(O)C>[NH2:3][C:2](=[CH:6][C:5](=[O:4])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])[CH3:1]

Participants

5

Reactant 2

HCID 179931875-Isopentyl-3-methylisoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 714061112-Amino-7-methyloct-2-en-4-one

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

3-Methyl-5-(3-methylbutyl)isoxazole (3.90 g, 25.5 mmol) [synthesis analogous to C. Kashima et al., Bull. Chem. Soc. Jpn. 46, 310-313 (1973)] is introduced into 80 ml of ethanol, platinum (IV) oxide catalyst (390 mg, 1.72 mmol) is added, and the mixture is then hydrogenated under atmospheric pressure hydrogen for 2 h (slightly exothermic reaction). The catalyst is filtered off, the filtrate is concentrated, and the residue is purified by chromatography on a Biotage 40M cartridge (mobile phase: isohexane/ethyl acetate 3:1). The product fractions are concentrated. The resulting residue is an oil, which crystallizes after a short time. Drying in vacuo results in 3.41 g (86% of theory) of the title compound.

Workup

  1. additionis added
  2. custom(slightly exothermic reaction)
  3. filtrationThe catalyst is filtered off
  4. concentrationthe filtrate is concentrated
  5. customthe residue is purified by chromatography on a Biotage 40M cartridge (mobile phase: isohexane/ethyl acetate 3:1)
  6. concentrationThe product fractions are concentrated
  7. customcrystallizes after a short time
  8. customDrying in vacuo

Sources & evidence

ORD record
ord-4aaa78e4f0294b5292b9b18c5568416e
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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