tert-butyl N-(oxolan-3-ylideneamino)carbamate

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

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

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

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

Procedure: t-butyl 2-[dihydrofuran-3(2H)-ylidene]hydrazinecarboxylate (17.26 g) was suspended in water (130 mL). Acetic acid (57.2 mL) was added to the suspension at room temperature. The mixture was stirred at room temperature for one hour. Sodium cyanoborohydride (5.36 g) was added to the solution in small portions. The mixed solution was stirred at room temperature for two hours. The reaction mixture was cooled to 0° C. The reaction mixture was neutralized by adding a 5 N aqueous sodium hydroxide solution. The mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5% methanol/ethyl acetate). The title compound (15.3 g) was obtained. The mixed solution was stirred at room temperature for two hours The reaction mixture was cooled to 0° C The mixture was extracted with chloroform The organic layer was dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (5% methanol/ethyl acetate)

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

Procedure: 3-oxotetrahydrofuran (10.38 g) was dissolved in methanol (200 mL), and t-butyl carbazate (17.53 g) was added to the solution. The mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated to give the title compound (27.3 g). 1H-NMR (400 MHz, CDCl3) δ (ppm): 1.52 (s, 9H), 2.46 (t, J=6.9 Hz, al), 4.10 (t, J=6.9 Hz, 2H), 4.33 (s, 2H). The reaction mixture was concentrated

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

Procedure: 3-oxotetrahydrofuran (10.38 g) was dissolved in methanol (200 mL), and t-butyl carbazate (17.53 g) was added to the solution. The mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated to give the title compound (27.3 g). 1H-NMR (400 MHz, CDCl3) δ (ppm): 1.52 (s, 9H), 2.46 (t, J=6.9 Hz, al), 4.10 (t, J=6.9 Hz, 2H), 4.33 (s, 2H). The reaction mixture was concentrated

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

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

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

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

Procedure: t-butyl 2-[dihydrofuran-3(2H)-ylidene]hydrazinecarboxylate (17.26 g) was suspended in water (130 mL). Acetic acid (57.2 mL) was added to the suspension at room temperature. The mixture was stirred at room temperature for one hour. Sodium cyanoborohydride (5.36 g) was added to the solution in small portions. The mixed solution was stirred at room temperature for two hours. The reaction mixture was cooled to 0° C. The reaction mixture was neutralized by adding a 5 N aqueous sodium hydroxide solution. The mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5% methanol/ethyl acetate). The title compound (15.3 g) was obtained. The mixed solution was stirred at room temperature for two hours The reaction mixture was cooled to 0° C The mixture was extracted with chloroform The organic layer was dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (5% methanol/ethyl acetate)

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

Procedure: 3-oxotetrahydrofuran (10.38 g) was dissolved in methanol (200 mL), and t-butyl carbazate (17.53 g) was added to the solution. The mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated to give the title compound (27.3 g). 1H-NMR (400 MHz, CDCl3) δ (ppm): 1.52 (s, 9H), 2.46 (t, J=6.9 Hz, al), 4.10 (t, J=6.9 Hz, 2H), 4.33 (s, 2H). The reaction mixture was concentrated