Iodoethane → HCID 86713365, compound

HRID 928066Notes

Reaction equation

HRID 928066 reaction equation
I[CH2:2][CH3:3].[NH:4]1[CH2:8][CH2:7][C@H:6]([CH2:9][C:10]#[N:11])[CH2:5]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:2]([N:4]1[CH2:8][CH2:7][C@H:6]([CH2:9][C:10]#[N:11])[CH2:5]1)[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 86713366HCID 86713366, compound2×

Product 1

HCID 86713365HCID 86713365, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Iodoethane (6.46 g) was added in portions to a cooled mixture of 2-((R)-pyrrolidin-3-yl)acetonitrile (Intermediate 210, 4.6 g) and potassium carbonate (8.6 g) in acetonitrile (30 mL) at 0° C. The mixture was stirred for 3 hours at 0° C. then concentrated under vacuum. The residue was partitioned between water and DCM. The organic layer was washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give 2-((R)-1-ethylpyrrolidin-3-yl)acetonitrile (2.1 g) as a colourless liquid which was used without further characterisation.

Workup

  1. concentrationthen concentrated under vacuum
  2. customThe residue was partitioned between water and DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-20e3ce84de42430f8121221bbaca8a6e
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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