Acetic Acid → (4-Propylamino-butyl)-carbamic acid t-butyl ester

HRID 2080873Notes

Reaction equation

HRID 2080873 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.C([BH3-])#N.[Na+].[CH:22](=O)[CH2:23][CH3:24]>CO>[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:22][CH2:23][CH3:24])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 86071285(4-Propylamino-butyl)-carbamic acid t-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (6.0 ml), (4-amino-butyl)-carbamic acid t-butyl ester (400.0 mg) was dissolved. After acetic acid (0.12 ml) and sodium cyanoborohydride (172.5 mg) were added to the solution, propionaldehyde (0.155 ml) was dropped thereto and the whole was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off and the residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (339.6 mg) as a colorless oily substance.

Workup

  1. additionwas dropped
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. dissolutionthe residue was dissolved in chloroform
  5. washwashed with a 1 mol/l sodium hydroxide aqueous solution
  6. extractionfollowed by extraction with chloroform
  7. washThe organic layer was washed with a saturated saline solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. distillationthe solvent was distilled off
  11. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5193be0848cd462da725fd9656cc0806
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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