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Acetic Acid → Tert-butyl 1-benzyl-8-ethylamino-1,2,3,4-tetrahydro-2-oxoquinolin-3-ylcarbamate

HRID 2070127
Notes
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Reaction equation

HRID 2070127 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9](=[O:19])[CH:8]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:7]2.[CH:28](=O)[CH3:29].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:12]([N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][CH2:28][CH3:29])[CH2:7][CH:8]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[C:9]1=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59620406Tert-butyl 8-amino-1-benzyl-1,2,3,4-tetrahydro-2-oxoquinolin-3-ylcarbamate

Product 1

HCID 59620343Tert-butyl 1-benzyl-8-ethylamino-1,2,3,4-tetrahydro-2-oxoquinolin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

tert-Butyl 8-amino-1-benzyl-1,2,3,4-tetrahydro-2-oxoquinolin-3-ylcarbamate (1.0 g) was dissolved in methanol (10 mL), and acetaldehyde (599 mg), acetic acid (10 mg), and sodium cyanoborohydride (171 mg) were sequentially added to the solution under cooling on ice. The mixture was stirred at room temperature for 30 minutes, and the reaction mixture was concentrated under reduced pressure. The thus-recovered residue was dissolved in ethyl acetate, and the solution was sequentially washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution. The organic layer was dried over sodium sulfate, and solvent was evaporated under reduced pressure. The recovered residue was purified through silica gel column chromatography (ethyl acetate: n-hexane=1:3), whereby the title compound (600 mg) was yielded.

Workup

  1. temperatureunder cooling on ice
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe thus-recovered residue was dissolved in ethyl acetate
  4. washthe solution was sequentially washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  5. dry with materialThe organic layer was dried over sodium sulfate, and solvent
  6. customwas evaporated under reduced pressure
  7. customThe recovered residue was purified through silica gel column chromatography (ethyl acetate: n-hexane=1:3), whereby the title compound (600 mg)
  8. customwas yielded

Sources & evidence

ORD record
ord-6fccba938ebf4986a6f22190b5251d71
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08299255B2

Reaction notes

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