4-Pentenal → HCID 69343188, compound

HRID 855175Notes

Reaction equation

HRID 855175 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:13](=O)[CH2:14][CH2:15][CH:16]=[CH2:17].[BH4-].[Na+]>CO.Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][CH2:17][CH2:16][CH2:15][CH:14]=[CH2:13])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 164184-PentenalHCID 27356554-tert-ButylbenzylamineHCID 4311764Sodium borohydride2×

Product 1

HCID 69343188HCID 69343188, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

0.44 ml of 4-tert-butylbenzylamine (2.5 mmol) and 0.414 ml of pent-4-enal (3.75 mmol) were dissolved in 7.5 ml methanol at rt and then refluxed for 1.5 h. After cooling down to rt, 114 mg (3 mmol) of sodium borohydride were added and after stirring for 15 min at rt, the reaction mixture was then refluxed for 2¼ h. After cooling down to rt again 114 mg of sodium borohydride were added and the mixture was again refluxed for additional 1¼ h. After cooling down to rt, the reaction mixture was treated with 5 drops 1 N HCl and concentrated in vacuo. The residue was diluted with water/EtOAc. After separation of the organic phase, the aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered off and concentrated in vacuo. The residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:1) to give 172 mg light yellow oil (29%). MS (ISP) 232.3 (M+H)+.

Workup

  1. temperaturerefluxed for 1.5 h
  2. temperaturethe reaction mixture was then refluxed for 2¼ h
  3. additionwere added
  4. temperaturethe mixture was again refluxed for additional 1¼ h
  5. temperatureAfter cooling down to rt
  6. concentrationconcentrated in vacuo
  7. additionThe residue was diluted with water/EtOAc
  8. customAfter separation of the organic phase
  9. extractionthe aqueous phase was extracted with EtOAc
  10. washthe combined organic phases were washed with brine
  11. dry with materialdried with magnesium sulfate
  12. filtrationfiltered off
  13. concentrationconcentrated in vacuo
  14. customThe residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:1)

Sources & evidence

ORD record
ord-a7a865d8686346c3951cdb9ad5376a97
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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