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 417687Notes

Reaction equation

HRID 417687 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]

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 6228DimethylformamideSolventHCID 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-7e614a1aa7c74a349fb12928377753d8
Source dataset
uspto-grants-2012_01
Patent number
US08088368B2

Reaction notes

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