5-NORBONENE-2-METHANAMINE

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A three-neck flask is equipped with mechanical stirrer, reflux condenser and dropping funnel. The flask is charged under N2, with 42 ml of a 1.0 M solution of lithium aluminum hydride in anhydrous ether (42 mmol). A solution of 5 g of 5-Norbornene-2-carbonitrile (bicyclo[2.2.1]hept-5-ene-2-carbonitrile) in 45 ml of ether (42 mmol, 1.0 M) is added dropwise through the addition funnel at a rate that allows a gentle reflux. After one hour, the mixture is cooled to 0° C. and water is added dropwise until hydrogen gas liberation is no longer observed. To this, 100 ml of 20% sodium potassium tartrate is added and produces a clear solution. The reaction solution is transferred to a separatory funnel, and the aqueous phase is collected and washed with 3×50 ml portions of ether. The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil. This product is further distilled under reduced pressure to yield a clear oil. A three-neck flask is equipped with mechanical stirrer reflux condenser produces a clear solution The reaction solution is transferred to a separatory funnel the aqueous phase is collected washed with 3×50 ml portions of ether The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil This product is further distilled under reduced pressure to yield a clear oil

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A three-neck flask is equipped with mechanical stirrer, reflux condenser and dropping funnel. The flask is charged under N2, with 42 ml of a 1.0 M solution of lithium aluminum hydride in anhydrous ether (42 mmol). A solution of 5 g of 5-Norbornene-2-carbonitrile (bicyclo[2.2.1]hept-5-ene-2-carbonitrile) in 45 ml of ether (42 mmol, 1.0 M) is added dropwise through the addition funnel at a rate that allows a gentle reflux. After one hour, the mixture is cooled to 0° C. and water is added dropwise until hydrogen gas liberation is no longer observed. To this, 100 ml of 20% sodium potassium tartrate is added and produces a clear solution. The reaction solution is transferred to a separatory funnel, and the aqueous phase is collected and washed with 3×50 ml portions of ether. The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil. This product is further distilled under reduced pressure to yield a clear oil. A three-neck flask is equipped with mechanical stirrer reflux condenser produces a clear solution The reaction solution is transferred to a separatory funnel the aqueous phase is collected washed with 3×50 ml portions of ether The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil This product is further distilled under reduced pressure to yield a clear oil

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A three-neck flask is equipped with mechanical stirrer, reflux condenser and dropping funnel. The flask is charged under N2, with 42 ml of a 1.0 M solution of lithium aluminum hydride in anhydrous ether (42 mmol). A solution of 5 g of 5-Norbornene-2-carbonitrile (bicyclo[2.2.1]hept-5-ene-2-carbonitrile) in 45 ml of ether (42 mmol, 1.0 M) is added dropwise through the addition funnel at a rate that allows a gentle reflux. After one hour, the mixture is cooled to 0° C. and water is added dropwise until hydrogen gas liberation is no longer observed. To this, 100 ml of 20% sodium potassium tartrate is added and produces a clear solution. The reaction solution is transferred to a separatory funnel, and the aqueous phase is collected and washed with 3×50 ml portions of ether. The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil. This product is further distilled under reduced pressure to yield a clear oil. A three-neck flask is equipped with mechanical stirrer reflux condenser produces a clear solution The reaction solution is transferred to a separatory funnel the aqueous phase is collected washed with 3×50 ml portions of ether The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil This product is further distilled under reduced pressure to yield a clear oil

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

Procedure: An oven-dried, nitrogen-flushed 1 L round bottom flask equipped with an addition funnel, nitrogen inlet, reagent inlet, and a teflon-coated stir bar was charged with 116.3 g 5-aminomethylnorbornene (0.944 mol,) 95.5 g triethylamine (0.944 mol,) and 1 L dichloromethane. The addition funnel was charged with 121.4 g ethanesulfonyl chloride (0.944 mol,) and 500 ml dichloromethane. The contents of the addition funnel were added dropwise to the flask over the course of approx. two hours. During this time, the reaction warmed gradually and finally began a gentle reflux. The reaction was left to stir for approx. 24 hours. The mixture was transferred into a separatory funnel, and the organic layer was washed twice with 300 ml water, 2× with 300 mL dilute sodium bicarbonate, and twice more with 300 ml water. The organic layer was dried over magnesium sulfate, then concentrated to yield an oil. Attempts to crystallize the oil from hexane:ethyl acetate failed. Silica gel column chromatography using hexane:ethyl acetate (60:40) as the eluent gave a clear, straw-colored oil that was further purified by vacuum distillation (140° C. at 5 microns of Hg) to provide 170 g of the desired ethanesulfonamide as a mixture of isomers. The product was identified by 1H and 13C NMR and IR spectroscopy. An oven-dried, nitrogen-flushed 1 L round bottom flask equipped with an addition funnel, nitrogen inlet, reagent inlet, and a teflon-coated stir bar The contents of the addition funnel were added dropwise to the flask over the course of approx. two hours During this time, the reaction warmed gradually The reaction was left The mixture was transferred into a separatory funnel the organic layer was washed twice with 300 ml water, 2× with 300 mL dilute sodium bicarbonate The organic layer was dried over magnesium sulfate concentrated to yield an oil to crystallize the oil from hexane gave a clear, straw-colored oil that was further purified by vacuum distillation (140° C. at 5 microns of Hg)

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

Procedure: An oven-dried, nitrogen-flushed 1 L round bottom flask equipped with an addition funnel, nitrogen inlet, reagent inlet, and a teflon-coated stir bar was charged with 116.3 g 5-aminomethylnorbornene (0.944 mol,) 95.5 g triethylamine (0.944 mol,) and 1 L dichloromethane. The addition funnel was charged with 121.4 g ethanesulfonyl chloride (0.944 mol,) and 500 ml dichloromethane. The contents of the addition funnel were added dropwise to the flask over the course of approx. two hours. During this time, the reaction warmed gradually and finally began a gentle reflux. The reaction was left to stir for approx. 24 hours. The mixture was transferred into a separatory funnel, and the organic layer was washed twice with 300 ml water, 2× with 300 mL dilute sodium bicarbonate, and twice more with 300 ml water. The organic layer was dried over magnesium sulfate, then concentrated to yield an oil. Attempts to crystallize the oil from hexane:ethyl acetate failed. Silica gel column chromatography using hexane:ethyl acetate (60:40) as the eluent gave a clear, straw-colored oil that was further purified by vacuum distillation (140° C. at 5 microns of Hg) to provide 170 g of the desired ethanesulfonamide as a mixture of isomers. The product was identified by 1H and 13C NMR and IR spectroscopy. An oven-dried, nitrogen-flushed 1 L round bottom flask equipped with an addition funnel, nitrogen inlet, reagent inlet, and a teflon-coated stir bar The contents of the addition funnel were added dropwise to the flask over the course of approx. two hours During this time, the reaction warmed gradually The reaction was left The mixture was transferred into a separatory funnel the organic layer was washed twice with 300 ml water, 2× with 300 mL dilute sodium bicarbonate The organic layer was dried over magnesium sulfate concentrated to yield an oil to crystallize the oil from hexane gave a clear, straw-colored oil that was further purified by vacuum distillation (140° C. at 5 microns of Hg)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A three-neck flask is equipped with mechanical stirrer, reflux condenser and dropping funnel. The flask is charged under N2, with 42 ml of a 1.0 M solution of lithium aluminum hydride in anhydrous ether (42 mmol). A solution of 5 g of 5-Norbornene-2-carbonitrile (bicyclo[2.2.1]hept-5-ene-2-carbonitrile) in 45 ml of ether (42 mmol, 1.0 M) is added dropwise through the addition funnel at a rate that allows a gentle reflux. After one hour, the mixture is cooled to 0° C. and water is added dropwise until hydrogen gas liberation is no longer observed. To this, 100 ml of 20% sodium potassium tartrate is added and produces a clear solution. The reaction solution is transferred to a separatory funnel, and the aqueous phase is collected and washed with 3×50 ml portions of ether. The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil. This product is further distilled under reduced pressure to yield a clear oil. A three-neck flask is equipped with mechanical stirrer reflux condenser produces a clear solution The reaction solution is transferred to a separatory funnel the aqueous phase is collected washed with 3×50 ml portions of ether The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil This product is further distilled under reduced pressure to yield a clear oil

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A three-neck flask is equipped with mechanical stirrer, reflux condenser and dropping funnel. The flask is charged under N2, with 42 ml of a 1.0 M solution of lithium aluminum hydride in anhydrous ether (42 mmol). A solution of 5 g of 5-Norbornene-2-carbonitrile (bicyclo[2.2.1]hept-5-ene-2-carbonitrile) in 45 ml of ether (42 mmol, 1.0 M) is added dropwise through the addition funnel at a rate that allows a gentle reflux. After one hour, the mixture is cooled to 0° C. and water is added dropwise until hydrogen gas liberation is no longer observed. To this, 100 ml of 20% sodium potassium tartrate is added and produces a clear solution. The reaction solution is transferred to a separatory funnel, and the aqueous phase is collected and washed with 3×50 ml portions of ether. The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil. This product is further distilled under reduced pressure to yield a clear oil. A three-neck flask is equipped with mechanical stirrer reflux condenser produces a clear solution The reaction solution is transferred to a separatory funnel the aqueous phase is collected washed with 3×50 ml portions of ether The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil This product is further distilled under reduced pressure to yield a clear oil

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A three-neck flask is equipped with mechanical stirrer, reflux condenser and dropping funnel. The flask is charged under N2, with 42 ml of a 1.0 M solution of lithium aluminum hydride in anhydrous ether (42 mmol). A solution of 5 g of 5-Norbornene-2-carbonitrile (bicyclo[2.2.1]hept-5-ene-2-carbonitrile) in 45 ml of ether (42 mmol, 1.0 M) is added dropwise through the addition funnel at a rate that allows a gentle reflux. After one hour, the mixture is cooled to 0° C. and water is added dropwise until hydrogen gas liberation is no longer observed. To this, 100 ml of 20% sodium potassium tartrate is added and produces a clear solution. The reaction solution is transferred to a separatory funnel, and the aqueous phase is collected and washed with 3×50 ml portions of ether. The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil. This product is further distilled under reduced pressure to yield a clear oil. A three-neck flask is equipped with mechanical stirrer reflux condenser produces a clear solution The reaction solution is transferred to a separatory funnel the aqueous phase is collected washed with 3×50 ml portions of ether The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil This product is further distilled under reduced pressure to yield a clear oil

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A three-neck flask is equipped with mechanical stirrer, reflux condenser and dropping funnel. The flask is charged under N2, with 42 ml of a 1.0 M solution of lithium aluminum hydride in anhydrous ether (42 mmol). A solution of 5 g of 5-Norbornene-2-carbonitrile (bicyclo[2.2.1]hept-5-ene-2-carbonitrile) in 45 ml of ether (42 mmol, 1.0 M) is added dropwise through the addition funnel at a rate that allows a gentle reflux. After one hour, the mixture is cooled to 0° C. and water is added dropwise until hydrogen gas liberation is no longer observed. To this, 100 ml of 20% sodium potassium tartrate is added and produces a clear solution. The reaction solution is transferred to a separatory funnel, and the aqueous phase is collected and washed with 3×50 ml portions of ether. The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil. This product is further distilled under reduced pressure to yield a clear oil. A three-neck flask is equipped with mechanical stirrer reflux condenser produces a clear solution The reaction solution is transferred to a separatory funnel the aqueous phase is collected washed with 3×50 ml portions of ether The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil This product is further distilled under reduced pressure to yield a clear oil