Sodium Iodide → HCID 54123030, compound

HRID 439574Notes

Reaction equation

HRID 439574 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([OH:20])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])=[CH:4][CH:3]=1.Br[CH2:22][CH2:23][CH2:24][CH2:25]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O>[OH:20][C@H:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:3][CH:4]=1)[C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 54490020HCID 54490020, compound

Product 1

HCID 54123030HCID 54123030, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The suspended solution of benzyl (R)-3-(4-aminophenyl)-2-hydroxypropionate(1.53 g), 1,4-dibromobutane (0.61 ml),potassium carbonate (2.07 g) and sodium iodide (0.37 g) indimethylformamide (5 ml) were stirred at room temperature for 71 hours. To the solution was added water (50 ml) and extracted withether (50 ml, 25 ml×2). After the ether layer was washed withsaturated brine, it was dried over anhydrous sodium sulfate. Thesolvent was evaporated in vacuo, the resultant crude product waspurified by silica gel column chromatography, and eluted withmixture of hexane and ethyl acetate (4:1, v/v). The fractionscontaining the desired product were combined and evaporated invacuo to obtain benzyl (R)-2-hydroxy-3-(4-pyrrolidinophenyl)propionate (1.35 g).

Workup

  1. extractionextracted withether (50 ml, 25 ml×2)
  2. washAfter the ether layer was washed
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customThesolvent was evaporated in vacuo
  5. washeluted withmixture of hexane and ethyl acetate (4:1
  6. customevaporated invacuo

Sources & evidence

ORD record
ord-9df65950c98a44c6a64f15035fda7e18
Source dataset
uspto-grants-1996_05
Patent number
US05514773

Reaction notes

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