3-Bromothiophene → HCID 67256873, compound

HRID 2371038Notes

Reaction equation

HRID 2371038 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[O:7]=[C:8]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]1>CCOCC>[OH:7][C:8]1([C:2]2[CH:6]=[CH:5][S:4][CH:3]=2)[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]1

Participants

4

Reactant 2

HCID 133833-BromothiopheneHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylate

Product 1

HCID 67256873HCID 67256873, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-65 °C

Procedure

To a solution of 3-bromothiophene (10 g, 61.8 mmol) in dry ether (200 mL) at −65° C. under N2 was added n-BiLi dropwise. After stirring at −65° C. for 1 h, tert-butyl 3-oxopyrrolidine-1-carboxylate (13.7 g, 74.2 mmol) in dry ether (80 mL) was added dropwise. After addition, the reaction mixture was warmed to 0° C. and stirred for 3 h. The reacton was quenched with water and extracted with ether. The combined organic layer was washed with brine, and dried over anhydrous Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound (9.8 g, 59%).

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was warmed to 0° C.
  3. stirringstirred for 3 h
  4. customThe reacton was quenched with water
  5. extractionextracted with ether
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationAfter filtration and concentration
  9. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-cc52a598e7a74d0fa0ae2ce499b2eacd
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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