Acetonitrile → (S)-1-Benzyl-pyrrolidine-3-carbonitrile

HRID 2226260Notes

Reaction equation

HRID 2226260 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10](OS(C)(=O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](#[N:20])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([C:18]#[N:20])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 118072543-Pyrrolidinol, 1-(phenylmethyl)-, 3-methanesulfonate, (3R)-

Product 1

HCID 1515498(S)-1-Benzyl-pyrrolidine-3-carbonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 165872Tetrabutylammonium CyanideCatalyst

Conditions

Temperature
65 °C

Procedure

(R)-1-Benzyl-3-mesyloxypyrrolidine (5.0 g, 20 mmol) was dissolved in acetonitrile (6 mL) and tetrabutylammonium cyanide (11.1 g, 41.4 mmol) was added. The mixture was heated at 65° C. for 3 hours and then cooled to room temperature and extracted with ethyl ether (100 mL). The organic layer was washed with saturated NaHCO3 (2×50 mL), dried over MgSO4, and concentrated under reduced pressure to give (S)-1-benzyl-3-cyanopyrrolidine (3.1 g, 85%) as a yellow oil: VPC: 100%; 1HNMR (CDCl3, 60 MHz): δ1.9-2.4 (m, 2H), 2.5-3.1 (m, 5H), 3.60 (s, 2H), 7.30 (s, 5H).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl ether (100 mL)
  3. washThe organic layer was washed with saturated NaHCO3 (2×50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ec02f72ad3254d6d94e6735c37a11175
Source dataset
uspto-grants-1994_09
Patent number
US05347017

Reaction notes

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