4-tert-Butylbenzylamine → HCID 69342909, compound

HRID 855178Notes

Reaction equation

HRID 855178 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].[CH3:13][C:14]1[O:18][C:17]([CH:19]([CH3:23])[CH2:20][CH:21]=O)=[CH:16][CH:15]=1.[BH4-].[Na+]>CO.Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][CH2:21][CH2:20][CH:19]([C:17]2[O:18][C:14]([CH3:13])=[CH:15][CH:16]=2)[CH3:23])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 27356554-tert-ButylbenzylamineHCID 35780333-(5-Methyl-2-furyl)butanalHCID 4311764Sodium borohydride2×

Product 1

HCID 69342909HCID 69342909, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

0.26 ml of 4-tert-butylbenzylamine (1.5 mmol) and 346 mg of [rac]-3-(5-methyl-furan-2-yl)-butyraldehyde (2.25 mmol) were dissolved in 4.5 ml methanol at rt, and after stirring for 30 min at rt, were refluxed for 2.5 h. After cooling down to rt, 68 mg (1.8 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 68 mg of sodium borohydride were added and the mixture was again refluxed for additional 18 h. After cooling down to rt, the reaction mixture was treated with 3 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 1:2) to give 328 mg light yellow oil (73%). MS (ISP) 300.4 (M+H)+.

Workup

  1. temperaturewere refluxed for 2.5 h
  2. temperatureAfter cooling down to rt
  3. stirringafter stirring for 15 min at rt
  4. temperaturethe reaction mixture was then refluxed for 2¼ h
  5. additionwere added
  6. temperaturethe mixture was again refluxed for additional 18 h
  7. temperatureAfter cooling down to rt
  8. concentrationconcentrated in vacuo
  9. additionThe residue was diluted with water/EtOAc
  10. customAfter separation of the organic phase
  11. extractionthe aqueous phase was extracted with EtOAc
  12. washthe combined organic phases were washed with brine
  13. dry with materialdried with magnesium sulfate
  14. filtrationfiltered off
  15. concentrationconcentrated in vacuo
  16. customThe residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:2)

Sources & evidence

ORD record
ord-5eec37f4891d4afcb7c94fc78352a5f4
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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