Trifluoroacetic acid → (4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano(3,4-f)indolizine-3,6,10(4H)-trione

HRID 1633746Notes

Reaction equation

HRID 1633746 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([C@:10]1([OH:29])[C:22]2[CH:21]=[C:20]3[N:16]([CH2:17][CH2:18][C:19]43OCC[O:23]4)[C:15](=[O:27])[C:14]=2[CH2:13][O:12][C:11]1=[O:28])[CH3:9]>C(OCC)(=O)C>[CH2:8]([C@:10]1([OH:29])[C:22]2[CH:21]=[C:20]3[N:16]([CH2:17][CH2:18][C:19]3=[O:23])[C:15](=[O:27])[C:14]=2[CH2:13][O:12][C:11]1=[O:28])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10902872(4'S)-4'-Ethyl-7',8'-dihydro-4'-hydroxyspiro[1,3-dioxolane-2,6'(3'H)-[1H]pyrano[3,4-f]indolizine]-3',10'(4'H)-dione

Product 1

HCID 10220900(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano(3,4-f)indolizine-3,6,10(4H)-trioneYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 90 ml of 90% trifluoroacetic acid, 3.5 g of (4S)-4-ethyl-6,6-(ethylenedioxy)-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,10(4H)-dione were added at room temperature over 5 minutes, followed by Stirring at the same temperature for 30 minutes. After completion of the reaction, the solvent was removed under reduced pressure, followed by the thorough removal of the solvent by a vacuum pump. To the residue so obtained was added 20 ml of ethyl acetate. The crystals precipitated were collected by filtration, whereby 2.4 g of the title compound were obtained.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed under reduced pressure
  3. customfollowed by the thorough removal of the solvent by a vacuum pump
  4. customTo the residue so obtained
  5. customThe crystals precipitated
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-5c251ff74d6f499db609b6d601bccb5a
Source dataset
uspto-grants-2003_01
Patent number
US06504029B1

Reaction notes

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