Water → (S)-2-(1-Acetylpyrrolidin-2-yl)acetonitrile

HRID 928012Notes

Reaction equation

HRID 928012 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].Cl.[NH:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[CH2:11][C:12]#[N:13].C(N(CC)CC)C.O>C(Cl)Cl>[C:1]([N:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[CH2:11][C:12]#[N:13])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86713338(S)-2-(Pyrrolidin-2-yl)acetonitrile hydrochloride2×

Product 1

HCID 45085914(S)-2-(1-Acetylpyrrolidin-2-yl)acetonitrileYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (8.6 g) was added dropwise to a stirred, cooled solution of ((S)-pyrrolidin-2-yl)acetonitrile hydrochloride (Intermediate 138, 8.0 g) and triethylamine (16.5 g) in DCM (80 mL) while maintaining the temperature at 0° C. The resultant solution was stirred at 0° C. for 30 minutes. Water was added and the layers were separated. The aqueous layer was further extracted with DCM and the combined organic layers were washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by HPLC (C18) to give ((S)-1-acetylpyrrolidin-2-yl)acetonitrile (5.0 g) as a light yellow oil which was used directly without further characterisation.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was further extracted with DCM
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by HPLC (C18)

Sources & evidence

ORD record
ord-52eff4203e034be194c3927d86be1be4
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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