Potassium Carbonate → HCID 66625920, compound

HRID 2167264Notes

Reaction equation

HRID 2167264 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:12]=2)[C@@H:7]([O:19]C(=O)C2C=CC=CC=2)[CH2:6][C@@H:5]1[CH3:28])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:12]=2)[C@@H:7]([OH:19])[CH2:6][C@@H:5]1[CH3:28])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 66625202HCID 66625202, compound

Product 1

HCID 66625920HCID 66625920, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

[Step 3] 1.02 g of ethyl (2S,4S)-1-acetyl-4-benzoyloxy-2-methyl-1,2,3,4-tetrahydroquinoline-6-carboxylate was dissolved in 10 mL of ethanol, and 1.11 g of potassium carbonate was slowly added to the solution. The mixture was stirred for 18 hours at 50° C., subsequently solids were filtered off, and the filtrate was washed two times with chloroform. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by using silica gel chromatography (hexane:ethyl acetate=2:1→1:2). Thus, 346 mg (38.2%, 2 steps) of ethyl (2S,4S)-1-acetyl-4-hydroxyl-2-methyl-1,2,3,4-tetrahydroquinoline-6-carboxylate was obtained as a pale yellow oily substance.

Workup

  1. filtrationsubsequently solids were filtered off
  2. washthe filtrate was washed two times with chloroform
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe resulting residue was purified

Sources & evidence

ORD record
ord-2566228752a6486cbbc2e87607ce2462
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

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