Water → HCID 67256476, compound

HRID 2371041Notes

Reaction equation

HRID 2371041 reaction equation
[OH:1][C:2]1([C:14]2[CH:18]=[CH:17][S:16][C:15]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2O)[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.B(F)(F)F.O>C(Cl)Cl>[S:16]1[C:15]2[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:1][C:2]3([CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]3)[C:14]=2[CH:18]=[CH:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 6356Boron trifluorideHCID 67257290HCID 67257290, compound

Product 1

HCID 67256476HCID 67256476, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-hydroxy-3-(2-(2-hydroxyphenyl)thiophen-3-yl)pyrrolidine-1-carboxylate (4.4 g, 12.1 mmol) in DCM (25 mL) at 0° C. was added BF3 (1.6 g, 24.2 mmol) dropwise. After stirring overnight, the reacton mixture was treated with water and extracted with EtOAc several times. 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 (3.8 g, 92%).

Workup

  1. extractionextracted with EtOAc several times
  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-8effae5d12c44379aed50069ad19d42b
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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