Toluene → (R)-1-Benzyl-3-pyrrolidinecarbonitrile
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+].C1(C)C=CC=CC=1.[C:30](#[N:32])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[C:30]([C@@H:10]1[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1)#[N:32]Participants
6
Conditions
- Temperature
- 65 °C
Procedure
(3S)-1-Benzyl-3-mesyloxypyrrolidine (2.56 g) was dissolved in acetonitrile (3.6 mL). Tetrabutylammonium cyanide (4.95 g) was added to the solution, and the mixture was stirred at 65° C. for 6.5 hours. Saturated sodium hydrogencarbonate (13 mL) and toluene were added dropwise to the reaction mixture, whereby the organic layer was extracted. The organic layer was washed with water and then dried over sodium sulfate. The drying agent was removed through filtration, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography, to thereby give the target compound (1.42 g, yield 76.2%) as a pale yellow oil.
Workup
- extractionwas extracted
- washThe organic layer was washed with water
- dry with materialdried over sodium sulfate
- customThe drying agent was removed through filtration
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b2d4533320e94ab5b9f1e40fda0d8784
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07569599B2
Reaction notes
Loading…