1,2,3,5,6,7-hexahydropyrrolizine-8-carbonitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 8.5 ml of acetic acid introduced therein hydrogen chloride gas (400 mg, 11.0 mmol), 7a-cyano-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine (300 mg, 2.20 mmol, obtained in Example 1) and platinum oxide (30 mg) were added to stir under hydrogen gas atmosphere for 24 hours at 20° C. After removal of insoluble matters from the reaction mixture, the filtrate was concentrated, 0.5N NaOH (10 ml) was added to the residue, which was extracted with chloroform, the extract was dried over anhydrous sodium sulfate, concentrated, and distilled in vacuo to afford 188 mg of the desired compound (Yield: 61%). After removal of insoluble matters from the reaction mixture the filtrate was concentrated 0.5N NaOH (10 ml) was added to the residue, which was extracted with chloroform the extract was dried over anhydrous sodium sulfate concentrated distilled in vacuo

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

Procedure: A mixed solution of 2-amino-2-methylpropanenitrile (41.4 g, 492 mmol) and 1,7-dichloro-4-heptanone (30.0 g, 164 mmol) in 220 ml of 16% NH3 /MeOH solution was stirred for 24 hours at 20° C. The resulting reaction mixture was concentrated in vacuo to remove MeOH therefrom, added 0.1N NaOH to the residue, which was extracted with methylene chloride, and the extract was dried over anhydrous sodium sulfate, concentrated, and distilled in vacuo to afford 18.1 g of the desired compound (Yield: 82%). The resulting reaction mixture was concentrated in vacuo to remove MeOH added 0.1N NaOH to the residue, which was extracted with methylene chloride the extract was dried over anhydrous sodium sulfate concentrated distilled in vacuo

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of aceton cyanohydrin (2.3 g, 27 mmol) saturated with ammonia, 1,7-dichloro-4-heptanone (0.50 g, 2.7 mmol) was added dropwise at 20° C. The resulting solution was stirred for 48 hours at 20° C. under ammonia gas atmosphere. To the reaction mixture, 0.1N-NaOH was added to extract with methylene chloride. The extract was dried over anhydrous sodium sulfate, concentrated and distilled in vacuo to afford 0.33 g of the desired compound (Yield: 89%). to extract with methylene chloride The extract was dried over anhydrous sodium sulfate concentrated distilled in vacuo

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 8.5 ml of acetic acid introduced therein hydrogen chloride gas (400 mg, 11.0 mmol), 7a-cyano-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine (300 mg, 2.20 mmol, obtained in Example 1) and platinum oxide (30 mg) were added to stir under hydrogen gas atmosphere for 24 hours at 20° C. After removal of insoluble matters from the reaction mixture, the filtrate was concentrated, 0.5N NaOH (10 ml) was added to the residue, which was extracted with chloroform, the extract was dried over anhydrous sodium sulfate, concentrated, and distilled in vacuo to afford 188 mg of the desired compound (Yield: 61%). After removal of insoluble matters from the reaction mixture the filtrate was concentrated 0.5N NaOH (10 ml) was added to the residue, which was extracted with chloroform the extract was dried over anhydrous sodium sulfate concentrated distilled in vacuo

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 8.5 ml of acetic acid introduced therein hydrogen chloride gas (400 mg, 11.0 mmol), 7a-cyano-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine (300 mg, 2.20 mmol, obtained in Example 1) and platinum oxide (30 mg) were added to stir under hydrogen gas atmosphere for 24 hours at 20° C. After removal of insoluble matters from the reaction mixture, the filtrate was concentrated, 0.5N NaOH (10 ml) was added to the residue, which was extracted with chloroform, the extract was dried over anhydrous sodium sulfate, concentrated, and distilled in vacuo to afford 188 mg of the desired compound (Yield: 61%). After removal of insoluble matters from the reaction mixture the filtrate was concentrated 0.5N NaOH (10 ml) was added to the residue, which was extracted with chloroform the extract was dried over anhydrous sodium sulfate concentrated distilled in vacuo

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

Procedure: A mixed solution of 2-amino-2-methylpropanenitrile (41.4 g, 492 mmol) and 1,7-dichloro-4-heptanone (30.0 g, 164 mmol) in 220 ml of 16% NH3 /MeOH solution was stirred for 24 hours at 20° C. The resulting reaction mixture was concentrated in vacuo to remove MeOH therefrom, added 0.1N NaOH to the residue, which was extracted with methylene chloride, and the extract was dried over anhydrous sodium sulfate, concentrated, and distilled in vacuo to afford 18.1 g of the desired compound (Yield: 82%). The resulting reaction mixture was concentrated in vacuo to remove MeOH added 0.1N NaOH to the residue, which was extracted with methylene chloride the extract was dried over anhydrous sodium sulfate concentrated distilled in vacuo

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

Procedure: A mixed solution of 2-amino-2-methylpropanenitrile (41.4 g, 492 mmol) and 1,7-dichloro-4-heptanone (30.0 g, 164 mmol) in 220 ml of 16% NH3 /MeOH solution was stirred for 24 hours at 20° C. The resulting reaction mixture was concentrated in vacuo to remove MeOH therefrom, added 0.1N NaOH to the residue, which was extracted with methylene chloride, and the extract was dried over anhydrous sodium sulfate, concentrated, and distilled in vacuo to afford 18.1 g of the desired compound (Yield: 82%). The resulting reaction mixture was concentrated in vacuo to remove MeOH added 0.1N NaOH to the residue, which was extracted with methylene chloride the extract was dried over anhydrous sodium sulfate concentrated distilled in vacuo

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of aceton cyanohydrin (2.3 g, 27 mmol) saturated with ammonia, 1,7-dichloro-4-heptanone (0.50 g, 2.7 mmol) was added dropwise at 20° C. The resulting solution was stirred for 48 hours at 20° C. under ammonia gas atmosphere. To the reaction mixture, 0.1N-NaOH was added to extract with methylene chloride. The extract was dried over anhydrous sodium sulfate, concentrated and distilled in vacuo to afford 0.33 g of the desired compound (Yield: 89%). to extract with methylene chloride The extract was dried over anhydrous sodium sulfate concentrated distilled in vacuo

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of aceton cyanohydrin (2.3 g, 27 mmol) saturated with ammonia, 1,7-dichloro-4-heptanone (0.50 g, 2.7 mmol) was added dropwise at 20° C. The resulting solution was stirred for 48 hours at 20° C. under ammonia gas atmosphere. To the reaction mixture, 0.1N-NaOH was added to extract with methylene chloride. The extract was dried over anhydrous sodium sulfate, concentrated and distilled in vacuo to afford 0.33 g of the desired compound (Yield: 89%). to extract with methylene chloride The extract was dried over anhydrous sodium sulfate concentrated distilled in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of potassium cyanide (0.191 g, 2.86 mmol) in 1.0 ml of water was added over 20 minutes 0.284 g (1.35 mmol) of 1-azoniabicyclo[3.3.0]oct-1(5)-ene (Example 3). The mixture was stirred at 20° C. for 1 hour. To the reaction mixture was added 2 ml of water and extracted with methylene chloride (3×10 ml). The combined organic layers were dried over anhydrous sodium sulfate and the solvent was distilled out in vacuo to afford 171 mg (Yield: 93.3%) of the desired compound. extracted with methylene chloride (3×10 ml) The combined organic layers were dried over anhydrous sodium sulfate the solvent was distilled out in vacuo