Tetrahydrofuran → HCID 59590019, compound

HRID 1971554Notes

Reaction equation

HRID 1971554 reaction equation
O1CCCC1.[Br:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](=O)[CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:10]=[CH:11][CH:12]=1>CO>[Br:6][C:7]1[CH:8]=[C:9]([NH:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 660492HCID 660492, compound

Product 1

HCID 59590019HCID 59590019, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1M solution of BH3 in tetrahydrofuran (10 ml, 10 mmol) was added dropwise to N-(3-bromo-phenyl)-3-pyrrolidin-1-yl-propionamide (0.3 g, 1 mmol) and the solution was stirred overnight at reflux then subsequently hydrolysed by slow addition of excess of methanol and refluxing for a further 2 hours. The solvent was removed under reduced pressure and aqueous ammonium chloride was added. The aqueous phase was extracted twice with ethyl acetate and the organics were combined, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting residue was dissolved in methanol and loaded onto an SCX cartridge, which was washed with methanol and the product subsequently eluted with 2M ammonia in methanol. Removal of all solvents under rotary evaporation gave the desired product. Yield 0.23 g, 82%. LCMS method: 2, RT: 2.71 min; MI: 283-285 [M+1].

Workup

  1. temperatureat reflux
  2. temperaturerefluxing for a further 2 hours
  3. customThe solvent was removed under reduced pressure and aqueous ammonium chloride
  4. additionwas added
  5. extractionThe aqueous phase was extracted twice with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. dissolutionThe resulting residue was dissolved in methanol
  9. washwas washed with methanol
  10. washthe product subsequently eluted with 2M ammonia in methanol
  11. customRemoval of all solvents
  12. customunder rotary evaporation

Sources & evidence

ORD record
ord-d852a671955241348d6d45533e5fd3b0
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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