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Potassium Carbonate → (3aS,6aS)-ethyl 1-(3-(phenylsulfonyl)quinolin-8-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

HRID 2068134
Notes
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Reaction equation

HRID 2068134 reaction equation
F[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])=[CH:7]2.C(O[C@H]([C@@H](OC(=O)C1C=CC=CC=1)C(O)=O)C(O)=O)(=O)C1C=CC=CC=1.[NH:47]1[CH2:51][CH2:50][C@H:49]2[CH2:52][N:53]([C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH2:54][C@@H:48]12.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Na+].[Cl-]>[C:15]1([S:12]([C:8]2[CH:9]=[N:10][C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[CH:3][C:2]=3[N:47]2[CH2:51][CH2:50][C@H:49]3[CH2:52][N:53]([C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH2:54][C@@H:48]23)(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 162237668-Fluoro-3-(phenylsulfonyl)quinolineHCID 86647686(3aS,6aS)-ethyl hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (2R,3R)-2,3-bis(benzoyloxy)succinate

Product 1

HCID 25196275(3aS,6aS)-ethyl 1-(3-(phenylsulfonyl)quinolin-8-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

Reagents, catalysts & solvents 2

HCID 5234
Sodium Chloride
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 8-fluoro-3-(phenylsulfonyl)quinoline (100 mg, 0.348 mmol), (3aS,6aS)-ethyl hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (2R,3R)-2,3-bis(benzoyloxy)succinate (944 mg, 1.74 mmol) and K2CO3 (577 mg) in DMF (3 mL) was stirred under nitrogen and heated at 100° C. for 7 h. The cooled mixture was diluted with 10 mL of saturated NaCl and the resultant precipitate collected and dried to give the title compound.

Workup

  1. customthe resultant precipitate collected
  2. customdried

Sources & evidence

ORD record
ord-47581279f31a490f99ffb9ffde4d39a9
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08293913B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes