Trifluoroacetic acid → HCID 118598902, compound

HRID 1050426Notes

Reaction equation

HRID 1050426 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6](CC2C=CC(OC)=CC=2)[C:5]([C:18](=[O:32])[CH:19]([C:25]2(O)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:4]([CH3:33])[CH:3]=1.FC(F)(F)C(O)=O>ClCCCl>[Br:1][C:2]1[C:7](=[O:8])[N:6]2[C:5](=[C:4]([CH3:33])[CH:3]=1)[C:18](=[O:32])[CH:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:25]12[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118598578HCID 118598578, compound

Product 1

HCID 118598902HCID 118598902, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of ethyl 3-(5-bromo-1-(4-methoxybenzyl)-3-methyl-6-oxo-1,6-dihydropyridin-2-yl)-2-(1-hydroxycyclohexyl)-3-oxopropanoate (5, 1.0 mmol, 1.0 eq) in 1,2-dichloroethane (15 mL), add trifluoroacetic acid (10 mmol, 10 eq) and heat the reaction at 60° C. for 16 h. After completion, remove the solvent and quench the reaction with ammonia and extract with dichloromethane. Remove the solvent under reduced pressure and purify the crude using silica gel column chromatography to afford ethyl 6′-bromo-8′-methyl-1′,5′-dioxo-1′,5′-dihydro-2′H-spiro[cyclohexane-1,3′-indolizine]-2′-carboxylate (6).

Workup

  1. temperatureheat
  2. customthe reaction at 60° C. for 16 h
  3. customAfter completion, remove the solvent
  4. customquench
  5. customthe reaction with ammonia
  6. extractionextract with dichloromethane
  7. customRemove the solvent under reduced pressure
  8. custompurify the crude

Sources & evidence

ORD record
ord-4ac70c23338f465aa6fe267fe708c976
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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