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

HRID 2226258Notes

Reaction equation

HRID 2226258 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%; 1HNMR (CDCl3, 200 MHz): δ2.0-2.4 (m, 2H), 2.6-2.8 (m, 3H), 2.85-3.10 (m, 2H), 3.65 (s, 2H), 7.3 (m, 5H).

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-fa10cdb71bfc4ad88121f77450fce7e8
Source dataset
uspto-grants-1994_09
Patent number
US05347017

Reaction notes

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