Sodium Iodide → HCID 73045401, compound

HRID 1919521Notes

Reaction equation

HRID 1919521 reaction equation
Br[CH2:2][C@H:3]1[CH2:7][CH2:6][C@H:5]([CH2:8][CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])[O:4]1.[Na+].[I-].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C([O-])(O)=O.[Na+].[Na]>O.C1COCC1.CS(C)=O>[O:24]1[CH2:25][CH2:26][N:21]([CH2:2][CH:3]2[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][C:10]3[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=3[O:17][CH3:18])[O:4]2)[CH2:22][CH2:23]1

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 8083MorpholineHCID 516892Sodium Bicarbonate2×HCID 5360545SodiumHCID 86623856HCID 86623856, compound

Product 1

HCID 73045401HCID 73045401, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a flask under Ar was added trans-2-(bromomethyl)-5-(2′-methoxy-5′-fluorophenethyl)tetrahydrofuran (43 mg, 0.136 mmol), NaI (30 mg), morpholine (65 mg, 0.75 mmol), NaHCO3 (130 mg) and dry DMSO (2.5 mL) and dry THF (4 mL). The mixture thus obtained was heated to reflux under Ar(g) for 12 h. After it was cooled to room temperature, the reaction mixture was poured to a separatory funnel containing sodium bicarcarbonate aqueous solution (sat. NaHCO3:H2O=1:1, 30 mL). The organic function was extracted with ethyl acetate (3×30 mL) and the combined organic layers were washed with brine (30 mL) and dried over sodium sulfate. The solvent then was removed in vacuo and crude product thus obtained was purified by flash column chromatography (2% MeOH in CH2Cl2, 0.1% TEA, Rf=0.21) to give the product (29 mg, 66%) as an oil.

Workup

  1. customThe mixture thus obtained
  2. temperaturewas heated
  3. additionthe reaction mixture was poured to a separatory funnel
  4. extractionThe organic function was extracted with ethyl acetate (3×30 mL)
  5. washthe combined organic layers were washed with brine (30 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe solvent then was removed in vacuo and crude product
  8. customthus obtained
  9. customwas purified by flash column chromatography (2% MeOH in CH2Cl2, 0.1% TEA, Rf=0.21)

Sources & evidence

ORD record
ord-e8cbb68980504d1eb2cd4c05b9889e71
Source dataset
uspto-grants-2012_05
Patent number
US08168635B2

Reaction notes

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