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N-bromobutanimide → Pyrrolidine-1,2-dicarboxylic acid 2-[2-(5-bromo-3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl ester

HRID 71995
Notes
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Reaction equation

HRID 71995 reaction equation
[S:1]1[C:5]([C:6](=[O:23])[CH2:7][O:8][C:9]([CH:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:10])=[CH:4][CH:3]2[S:24][CH:25]=[CH:26][CH:2]12.[Br:27]N1C(=O)CCC1=O>CN(C=O)C.CCOC(C)=O>[C:19]([O:18][C:16]([N:12]1[CH2:13][CH2:14][CH2:15][CH:11]1[C:9]([O:8][CH2:7][C:6]([C:5]1[S:1][CH:2]2[CH:26]=[C:25]([Br:27])[S:24][CH:3]2[CH:4]=1)=[O:23])=[O:10])=[O:17])([CH3:20])([CH3:21])[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 66620078Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-[2-(3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-2-oxo-ethyl]ester

Product 1

HCID 66620153Pyrrolidine-1,2-dicarboxylic acid 2-[2-(5-bromo-3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl esterYield 66%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-[2-(3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-2-oxo-ethyl]ester (595 mg, 1.5 mmol) was dissolved in DMF (7.5 mL) and treated with N-bromosuccinimide (295 mg, 1.65 mmol). The reaction mixture was stirred for 4d at RT then diluted with EtOAc and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated. The crude residue was purified by silica column chromatography (20% to 50% EtOAc/Hex) to afford the title compound (469 mg, 66%).

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by silica column chromatography (20% to 50% EtOAc/Hex)

Sources & evidence

ORD record
ord-e2904203544f42fbaefaa7a5c5ff1067
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822430B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes