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

HRID 39215
Notes
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Reaction equation

HRID 39215 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

HCID 66794569Ethyl 3-(octahydroquinolin-1-yl)-3-oxopropionate

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

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. customare dried over anhydrous

Sources & evidence

ORD record
ord-7b31eb19252f4fb084552a23f4201ee8
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524894B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes