Sodium borohydride → 3-(2-Pyrrolidin-2-(r,s)-ylethyl)-benzonitrile

HRID 901335Notes

Reaction equation

HRID 901335 reaction equation
[N:1]1[CH2:5][CH2:4][CH2:3][C:2]=1[CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12].[BH4-].[Na+]>CCO>[NH:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 692552573-[2-(4,5-Dihydro-3H-pyrrol-2-yl)-ethyl]benzonitrile

Product 1

HCID 776287743-(2-Pyrrolidin-2-(r,s)-ylethyl)-benzonitrileYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A flask containing 3-[2-(4,5-Dihydro-3H-pyrrol-2-yl)-ethyl]benzonitrile (0.22 g, 1.11 mmol) and absolute EtOH (10 mL) was stirred under nitrogen at 0° C. To this was added NaBH4 (0.063 g, 1.66 mmol) in one portion and the reaction is warmed to room temperature and stirred 1 h. The reaction is concentrated and the residue diluted with H20 (15 mL). 1 N HCl (15 mL) is added and the solution is washed with ether. The aqueous phase is basified with solid sodium carbonate and extracted with EtOAc (3×25 mL). The combined organic extracts are dried over MgSO4 and concentrated to give the title compound as a yellow oil (0.10 g, 0.50 mmol). 1H NMR (CDCl3, 300 MHz) 7.55-7.30(m, 4H), 4.01, 3.82(two m, 1H), 3.66-3.22(m, 2H), 3.05-2.55(m, 2H), 2.33-1.60(m, 6H).

Workup

  1. temperaturethe reaction is warmed to room temperature
  2. stirringstirred 1 h
  3. concentrationThe reaction is concentrated
  4. additionthe residue diluted with H20 (15 mL)
  5. addition1 N HCl (15 mL) is added
  6. washthe solution is washed with ether
  7. extractionextracted with EtOAc (3×25 mL)
  8. dry with materialThe combined organic extracts are dried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-58e73b5518de4daa9f356029473ada2f
Source dataset
uspto-grants-2008_04
Patent number
US07361663B2

Reaction notes

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