Ethyl Acetate → 3-[(Octahydroquinoline-1-carbonyl)amino]propionic acid methyl ester

HRID 68329Notes

Reaction equation

HRID 68329 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:8])[CH2:5][CH2:6][NH2:7].Cl[C:10]([N:12]1[CH:21]2[CH:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:15][CH2:14][CH2:13]1)=[O:11].CCOC(C)=O>C1COCC1.CCN(CC)CC>[CH3:2][O:3][C:4](=[O:8])[CH2:5][CH2:6][NH:7][C:10]([N:12]1[CH:21]2[CH:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:15][CH2:14][CH2:13]1)=[O:11]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 189245821-Chlorocarbonyloctahydroquinoline

Product 1

HCID 667944273-[(Octahydroquinoline-1-carbonyl)amino]propionic acid methyl esterYield 67.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

0.5 g (3.5 mmol) of the 3-aminopropionic acid methyl ester hydrochloride are dissolved in 5 mL of anhydrous THF and 0.9 mL of Et3N. Once dissolved, 650 mg of 1-chlorocarbonyloctahydroquinoline are slowly added and it is refluxed for 18 h. AcOEt is then added and the resulting solution is sequentially washed with water, 1N HCl and brine. The organic phase is dried over anhydrous Na2SO4, it is filtered and the solvent is evaporated under reduced pressure yielding 580 mg of intermediate IIIb.1.

Workup

  1. dissolutionOnce dissolved
  2. temperatureit is refluxed for 18 h
  3. washthe resulting solution is sequentially washed with water, 1N HCl and brine
  4. dry with materialThe organic phase is dried over anhydrous Na2SO4, it
  5. filtrationis filtered
  6. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-32ee13e4c31e48fcbf57c4853a2e79be
Source dataset
uspto-grants-2014_09
Patent number
US08822452B2

Reaction notes

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