Water → HCID 67257288, compound

HRID 2371039Notes

Reaction equation

HRID 2371039 reaction equation
[OH:1][C:2]1([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.C1C(=O)N([Br:26])C(=O)C1.[O-]S([O-])=O.[Na+].[Na+].O>CC(O)=O.C(Cl)(Cl)Cl>[Br:26][C:15]1[S:16][CH:17]=[CH:18][C:14]=1[C:2]1([OH:1])[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:11])[CH3:12])=[O:8])[CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 67256873HCID 67256873, compound

Product 1

HCID 67257288HCID 67257288, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To a solution of tert-butyl 3-hydroxy-3-(thiophen-3-yl)pyrrolidine-1-carboxylate (5 g, 18.6 mmol) in AcOH (10 mL) and CHCl3 (10 mL) at 0° C. was added NBS (5.0 g, 27.9 mmol) in portions. After stirring for 3 h, the reaction mixture was treated with Na2SO3 and water, followed by extraction with EtOAc. 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 (5.4 g, 84%).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-a4cc3ca1c4424f1fa497b01e84f785b8
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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