3-Methylbutanal → HCID 23291924, compound

HRID 365515Notes

Reaction equation

HRID 365515 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)=[CH:11][CH:12]=2)[C:7]([CH3:27])([CH3:26])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH:28](=O)[CH2:29][CH:30]([CH3:32])[CH3:31].C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.C(#N)C>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:14]([CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[C:15]3[CH:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=3)=[CH:11][CH:12]=2)[C:7]([CH3:27])([CH3:26])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 115523-MethylbutanalHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 23291922HCID 23291922, compound2×

Product 1

HCID 23291924HCID 23291924, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

Ethyl 4-[(1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amino]benzoate (Compound 8, 37 mg, 0.10 mmol) was dissolved in a 10% acetic acid in acetonitrile solution (1.5 mL). The solution was treated with isovaleraldehyde (0.08 mL, 0.74 mmol) and then sodium cyanoborohydride (13 mg, 0.20 mmol) and the reaction mixture was stirred at room temperature for 5 hours. 1M aqueous NaOH was added until pH=6 and the solution was extracted with ether (2×), washed with brine, and dried (Na2SO4). The filtered solution was concentrated under reduced pressure and the residue purified by silica gel chromatography (5% ethyl acetate in hexanes) to give the title compound (20 mg, 45%) as an oil.

Workup

  1. extractionthe solution was extracted with ether (2×)
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationThe filtered solution was concentrated under reduced pressure
  5. customthe residue purified by silica gel chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2ee0eebdd1af42f9ab0ae589f0f5dd96
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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