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

HRID 129198

Reaction equation

HRID 129198 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%;

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-775f15c9248a45b3941a409cfadd43f9
Source dataset
uspto-grants-1995_11
Patent number
US05466828

Linked notes

Loading…