Water → Ethyl 3-(octahydroquinolin-1-yl)-3-oxopropionate

HRID 68328

Reaction equation

HRID 68328 reaction equation
CCN(CC)CC.Cl[C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[NH:17]1[CH:26]2[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]2)[CH2:20][CH2:19][CH2:18]1.O>CCOC(C)=O>[N:17]1([C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:26]2[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]2)[CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 92911DecahydroquinolineHCID 118931Ethyl 3-chloro-3-oxopropionate

Product 1

HCID 66794569Ethyl 3-(octahydroquinolin-1-yl)-3-oxopropionateYield 78.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3.38 mL of Et3N and 1.44 mL (11 mmol) of ethyl 3-chloro-3-oxopropionate are added to a solution of 1.5 mL (10 mmol) of decahydroquinoline in 100 mL of AcOEt. The resulting solution is kept under stirring at reflux for 10 h. Then water is added and the organic phase is separated, the aqueous phase is extracted once again with AcOEt. The organic phases are pooled and they are first washed with 5% solution of NaHCO3 and subsequently with brine, they are dried over anhydrous Na2SO4, they are filtered and the solvent is evaporated under reduced pressure. 2.0 g of a yellow oil are obtained. It is identified as intermediate IIIa.1. Method A: tr: 6.76 min; m/z: 268.

Workup

  1. temperatureat reflux for 10 h
  2. customthe organic phase is separated
  3. extractionthe aqueous phase is extracted once again with AcOEt
  4. washthey are first washed with 5% solution of NaHCO3 and subsequently with brine, they
  5. dry with materialare dried over anhydrous Na2SO4, they
  6. filtrationare filtered
  7. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-e6a5c0325d5a4f4c8690b3127b1584ef
Source dataset
uspto-grants-2014_09
Patent number
US08822452B2

Linked notes

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