Iodine → HCID 58017223, compound

HRID 661575Notes

Reaction equation

HRID 661575 reaction equation
Br[C:2]1[C:6]2[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[Mg].II.[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][C:24]([CH2:29][CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])([CH:27]=[O:28])[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>O1CCCC1>[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][C:24]([CH2:29][CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])([CH:27]([C:2]2[C:6]3[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=3[S:4][CH:3]=2)[OH:28])[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 807IodineHCID 5462224MagnesiumHCID 19800079138993-21-2HCID 58017254HCID 58017254, compound

Product 1

HCID 58017223HCID 58017223, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3-bromo-5-fluoro-benzothiophene (0.4 g, 1.73 mmoles), magnesium (0.051 g, 2.1 mmoles) and a few particles of iodine in anhydrous tetrahydrofuran (10 mil) was refluxed for 7 hours, and then cooled in an ice bath. To the reaction mixture was slowly added a solution of 3-(3,3-dimethyl-butyl)-3-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.39 g, 1.38 mmoles) in anhydrous tetrahydrofuran (9 mil). The reaction mixture was stirred at ice bath temperature for one hour and quenched with saturated aqueous ammonium chloride solution. The aqueous solution was extracted into ethylacetate which was washed with brine and dried over anhydrous sodium sulfate. After removal of drying agent, the organic solution was concentrated under reduced pressure. The residue was purified by silica gel chromatography (0 to 20% ethyl acetate in hexane) to yield 3-(3,3-dimethyl-butyl)-3-[(5-fluoro-benzo[b]thiophen-3-yl)-hydroxy-methyl]-pyrrolidine-1-carboxylic acid tert butyl ester as yellow foam (0.13 g, 21%), MS=436 [M+H]+.

Workup

  1. temperaturecooled in an ice bath
  2. customquenched with saturated aqueous ammonium chloride solution
  3. extractionThe aqueous solution was extracted into ethylacetate which
  4. washwas washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter removal
  7. customof drying agent
  8. concentrationthe organic solution was concentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (0 to 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-63b5d89a59ff46a7ab852cccb107b520
Source dataset
uspto-grants-2011_12
Patent number
US08084623B2

Reaction notes

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