2-[(2S)-1-methylpyrrolidin-2-yl]acetonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Raney-Ni (1.5 ml) was added to an EtOH (30 ml) solution of the 2-((2S)-1-methyl-5-thioxopyrrolidin-2-yl)ethanenitrile (940 mg, 6.1 mmols), and the mixture was heated for 24 hours under reflux (upon TCL, the starting materials had not completely disappeared). The inorganic matter was filtered off, and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (SiO2 40 g, MeOH—CHCl3 1:9 v/v) to obtain 2-((2S)-1-methylpyrrolidin-2-yl)ethanenitrile as a mixture (195 mg) with impurities difficult to separate. the mixture was heated for 24 hours under reflux (upon TCL The inorganic matter was filtered off the solvent was distilled off under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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°.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Raney-Ni (1.5 ml) was added to an EtOH (30 ml) solution of the 2-((2S)-1-methyl-5-thioxopyrrolidin-2-yl)ethanenitrile (940 mg, 6.1 mmols), and the mixture was heated for 24 hours under reflux (upon TCL, the starting materials had not completely disappeared). The inorganic matter was filtered off, and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (SiO2 40 g, MeOH—CHCl3 1:9 v/v) to obtain 2-((2S)-1-methylpyrrolidin-2-yl)ethanenitrile as a mixture (195 mg) with impurities difficult to separate. the mixture was heated for 24 hours under reflux (upon TCL The inorganic matter was filtered off the solvent was distilled off under reduced pressure