Tetrahydrofuran → HCID 59589731, compound

HRID 1971556Notes

Reaction equation

HRID 1971556 reaction equation
O1CCCC1.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=O)[CH:15]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH3:16])=[CH:9][CH:8]=1>CO>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:14][CH:15]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH3:16])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 13221932HCID 13221932, compound

Product 1

HCID 59589731HCID 59589731, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1M solution of BH3 in tetrahydrofuran (10 ml, 10 mmol) was added dropwise to N-(4-bromo-phenyl)-2-pyrrolidin-1-yl-propionamide (0.44 g, 1.48 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 reaction mixture was 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: 0.04 g, 10%. LCMS method: 2, RT: 3.07 min; MI: 283-285 [M+1].

Workup

  1. temperatureat reflux
  2. temperaturerefluxing for a further 2 hours
  3. washwas washed with methanol
  4. washthe product subsequently eluted with 2M ammonia in methanol
  5. customRemoval of all solvents
  6. customunder rotary evaporation

Sources & evidence

ORD record
ord-c3bea0f527f04b348fb581fc72843625
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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