tert-butyl N-(2-cyanoethyl)carbamate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (2-Cyano-ethyl)-carbamic acid tert-butyl ester (59.5 g, 0.35 mol) is dissolved in dry m-xylene 460 ml) and stirred at room temperature. Azidotributyltin (140 g, 0.42 mol) is added and the reaction mixture is heated to 115° C. overnight. On cooling to room temperature, the reaction mixture is quenched with 2M NaOH (500 ml), the layers are separated and the aqueous phase is acidified with 6M HCl to pH 2 resulting in a thick precipitate. DCM (500 ml) is added followed by IPA (50 ml) resulting in clear layers, the organic layer is separated and the aqueous is re-extracted with 9:1 DCM/IPA (2×250 ml). The organic layers are combined, washed with brine (500 ml), dried over MgSO4, filtered and concentrated in vacuo. The resulting solid is triturated with iso-hexanes (250 ml), stirred for 1 hour at room temperature then a further 1 hour at 5-10° C., filtered and dried under vacuum to afford the title compound. the reaction mixture is heated to 115° C. overnight On cooling to room temperature the reaction mixture is quenched with 2M NaOH (500 ml) the layers are separated resulting in a thick precipitate resulting in clear layers the organic layer is separated the aqueous is re-extracted with 9:1 DCM/IPA (2×250 ml) washed with brine (500 ml) dried over MgSO4 filtered concentrated in vacuo The resulting solid is triturated with iso-hexanes (250 ml) stirred for 1 hour at room temperature a further 1 hour at 5-10° C., filtered dried under vacuum

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (2-Cyano-ethyl)-carbamic acid tert-butyl ester (59.5 g, 0.35 mol) is dissolved in dry m-xylene 460 ml) and stirred at room temperature. Azidotributyltin (140 g, 0.42 mol) is added and the reaction mixture is heated to 115° C. overnight. On cooling to room temperature, the reaction mixture is quenched with 2M NaOH (500 ml), the layers are separated and the aqueous phase is acidified with 6M HCl to pH 2 resulting in a thick precipitate. DCM (500 ml) is added followed by IPA (50 ml) resulting in clear layers, the organic layer is separated and the aqueous is re-extracted with 9:1 DCM/IPA (2×250 ml). The organic layers are combined, washed with brine (500 ml), dried over MgSO4, filtered and concentrated in vacuo. The resulting solid is triturated with iso-hexanes (250 ml), stirred for 1 hour at room temperature then a further 1 hour at 5-10° C., filtered and dried under vacuum to afford the title compound. the reaction mixture is heated to 115° C. overnight On cooling to room temperature the reaction mixture is quenched with 2M NaOH (500 ml) the layers are separated resulting in a thick precipitate resulting in clear layers the organic layer is separated the aqueous is re-extracted with 9:1 DCM/IPA (2×250 ml) washed with brine (500 ml) dried over MgSO4 filtered concentrated in vacuo The resulting solid is triturated with iso-hexanes (250 ml) stirred for 1 hour at room temperature a further 1 hour at 5-10° C., filtered dried under vacuum

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Tert-butyl N-(2-cyanoethyl)carbamate (40 g; 235 mmol; 1 eq.) and hydroxylamine (41.6 ml; 705 mmol; 3 eq.) are dissolved in EtOH (800 ml). The resulting solution is heated under reflux for 2 hours. The reaction progression is followed by 1H NMR. After 2 hours, the reaction mixture is cooled down to RT, concentrated under high vacuum to afford the title compound as a white solid (47.5 g, 99%). The resulting solution is heated under reflux for 2 hours concentrated under high vacuum

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Tert-butyl N-(2-cyanoethyl)carbamate (40 g; 235 mmol; 1 eq.) and hydroxylamine (41.6 ml; 705 mmol; 3 eq.) are dissolved in EtOH (800 ml). The resulting solution is heated under reflux for 2 hours. The reaction is followed by NMR. The reaction mixture is then cooled down to RT, and concentrated under vacuum, affording the title compound as a white solid (47.5 g, 99%). The resulting solution is heated under reflux for 2 hours concentrated under vacuum

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (2-Cyano-ethyl)-carbamic acid tert-butyl ester (59.5 g, 0.35 mol) is dissolved in dry m-xylene 460 ml) and stirred at room temperature. Azidotributyltin (140 g, 0.42 mol) is added and the reaction mixture is heated to 115° C. overnight. On cooling to room temperature, the reaction mixture is quenched with 2M NaOH (500 ml), the layers are separated and the aqueous phase is acidified with 6M HCl to pH 2 resulting in a thick precipitate. DCM (500 ml) is added followed by IPA (50 ml) resulting in clear layers, the organic layer is separated and the aqueous is re-extracted with 9:1 DCM/IPA (2×250 ml). The organic layers are combined, washed with brine (500 ml), dried over MgSO4, filtered and concentrated in vacuo. The resulting solid is triturated with iso-hexanes (250 ml), stirred for 1 hour at room temperature then a further 1 hour at 5-10° C., filtered and dried under vacuum to afford the title compound. the reaction mixture is heated to 115° C. overnight On cooling to room temperature the reaction mixture is quenched with 2M NaOH (500 ml) the layers are separated resulting in a thick precipitate resulting in clear layers the organic layer is separated the aqueous is re-extracted with 9:1 DCM/IPA (2×250 ml) washed with brine (500 ml) dried over MgSO4 filtered concentrated in vacuo The resulting solid is triturated with iso-hexanes (250 ml) stirred for 1 hour at room temperature a further 1 hour at 5-10° C., filtered dried under vacuum

反応条件: temp:0.00; pressure:0.00; stir: