Potassium Carbonate → (3aS,6aS)-ethyl 1-(3-(phenylsulfonyl)quinolin-8-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate
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]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
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
- customthe resultant precipitate collected
- customdried
Sources & evidence
- ORD record
- ord-47581279f31a490f99ffb9ffde4d39a9
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293913B2
Reaction notes
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