Acetonitrile → (R)-1-Benzyl-3-pyrrolidinecarbonitrile

HRID 129196

Reaction equation

HRID 129196 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([O-])(O)=O.[Na+].[C:23](#[N:25])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:23]#[N:25])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 10934081(S)-1-Benzyl-3-mesyloxypyrrolidine

Product 1

HCID 1515497(R)-1-Benzyl-3-pyrrolidinecarbonitrileYield 85.6%

Reagents, catalysts & solvents 1

HCID 165872Tetrabutylammonium CyanideCatalyst

Conditions

Temperature
65 °C

Procedure

(S)-1-Benzyl-3-mesyloxypyrrolidine (264.3 g, 1.03 mol) was dissolved in acetonitrile (170 mL) and tetrabutylammonium cyanide (556 g, 2.07 mol) was added. The resulting mixture was heated at 65° C. for 2 days and then cooled to room temperature and saturated NaHCO3 (500 mL) added. The organic layer was separated and the aqueous layer extracted with toluene (600 mL and 400 mL). The combined organic layers were washed with water (4×500 mL) and concentrated under reduced pressure to give (R)-1-benzyl-3-cyanopyrrolidine as a brown oil (165 g, 85.6%): IR: 2239 cm-1 ; VPC: 97.0%;

Workup

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with toluene (600 mL and 400 mL)
  4. washThe combined organic layers were washed with water (4×500 mL)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a08583cdcccb404ba14394ae9aa4822b
Source dataset
uspto-grants-1995_11
Patent number
US05466828

Linked notes

Loading…