3-Methylbutanal → HCID 29545440, compound

HRID 855174Notes

Reaction equation

HRID 855174 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][CH:14]([CH3:18])[CH2:15][CH:16]=O.[BH4-].[Na+]>CO.Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][CH2:16][CH2:15][CH:14]([CH3:18])[CH3:13])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 115523-MethylbutanalHCID 27356554-tert-ButylbenzylamineHCID 4311764Sodium borohydride

Product 1

HCID 29545440HCID 29545440, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

0.44 ml of 4-tert-butylbenzylamine (2.5 mmol) and 0.414 ml of 3-methylbutyraldehyde (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 the reaction mixture was then refluxed for 1.5 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 458 mg light yellow oil (78%). MS (ISP) 234.3 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-f1343b676858490495e3d05ad4e17d86
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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