Isobutylamine → HCID 28428108, compound

HRID 1665025Notes

Reaction equation

HRID 1665025 reaction equation
[Br:1][C:2]1[O:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.[CH2:9]([NH2:13])[CH:10]([CH3:12])[CH3:11].[BH4-].[Na+]>CO>[Br:1][C:2]1[O:6][C:5]([CH2:7][NH:13][CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 6003285-Bromofuran-2-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 28428108HCID 28428108, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 5-bromo-2-furaldehyde (500 mg) in methanol (5 mL) was added isobutylamine (209 mg). The mixture was stirred overnight at r.t. Sodium borohydride (162 mg) was added and the mixture was stirred for 2 h. The solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure to give the crude (5-bromo-furan-2-ylmethyl)-isobutyl-amine (686 mg) as a colorless oil which was used in the next step without further purification.

Workup

  1. stirringthe mixture was stirred for 2 h
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2b8aca3ef17f4017890de2b03affe842
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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