Sodium ethoxide → HCID 66625237, compound

HRID 2167275Notes

Reaction equation

HRID 2167275 reaction equation
C([O:9][C@@H:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:18]=2)[N:13]([C:26](=[O:28])[CH3:27])[C@@H:12]([CH3:29])[CH2:11]1)(=O)C1C=CC=CC=1.[O-]CC.[Na+]>C(O)C>[C:26]([N:13]1[C:14]2[C:19](=[CH:18][C:17]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)=[CH:16][CH:15]=2)[C@@H:10]([OH:9])[CH2:11][C@@H:12]1[CH3:29])(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 66625684HCID 66625684, compound

Product 1

HCID 66625237HCID 66625237, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[Step 2] 180.6 mg of (2S,4S)-1-acetyl-2-methyl-6-morpholino-1,2,3,4-tetrahydroquinolin-4-yl benzoate was dissolved in 2 mL of ethanol, and 30.7 mg of sodium ethoxide was added to the solution. The mixture was stirred for 2 hours at room temperature. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, water was added thereto, and the mixture was extracted three times with ethyl acetate. The extraction product was washed with saturated brine, dehydrated over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (ethyl acetate:hexane=1:2). Thus, 97.8 mg (67.4%) of (2S,4S)-1-acetyl-4-hydroxyl-2-methyl-6-morpholino-1,2,3,4-tetrahydroquinoline was obtained as a white solid.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure, water
  3. additionwas added
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. washThe extraction product was washed with saturated brine
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified

Sources & evidence

ORD record
ord-e1fa2106cba24427bb5aabfde56dc84c
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

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