Methanol → [(2S)-1-Methylpyrrolidin-2-yl]acetonitrile
Reaction equation
[C:1]1([C:15]([O-])=[C:11]([N+:12]([O-])=O)[CH:10]=[C:6]([N+:7]([O-])=O)[CH:5]=1)[N+]([O-])=O.[CH3:17]O>>[CH3:17][N:12]1[CH2:5][CH2:1][CH2:15][C@H:11]1[CH2:10][C:6]#[N:7]Participants
Procedure
To a solution of 7.0 g (0.041 mol) of (S)-1-methyl-2-chloromethylpyrrolidine.HCl in 35 ml of 80% aq. ethanol at 0° was added in portions a solution of 3.81 g (0.045 mol) of sodium bicarbonate in 50 ml of water. The mixture was stirred at 0° for 15 min., followed by the addition of a solution of 2.52 g (0.052 mol) of sodium cyanide in 65 ml of 80% aq. ethanol. This mixture was refluxed for 30 min. The resultant solution was cooled, evaporated to a small volume, and extracted with ether (2×25 ml). The combined ethereal layer was dried wtih magnesium sulfate and evaporated to a clear, brown oil. Bulb-to-bulb distillation [oven temp 40°-55° (0.25 torr)] yielded 2.62 g (51%) of the product, a clear, colorless, mobile oil: [α]D20 =-32.5°, c=2.57, methanol; picrate, mp 175° -178°.
Sources & evidence
- ORD record
- ord-55c49d58b509479e8259e2d7c2a6858a
- Source dataset
- uspto-grants-1982_03
- Patent number
- US04321387
Reaction notes
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