benzyl 1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylate

反応条件: temp:0.00; pressure:0.00; stir:

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: To a well-stirred and ice-cooled solution of 1,4-dioxa-8-azaspiro[4,5]decane (34.9 mmol, 5 g) in dichloromethane (200 mL) under an argon atmosphere, is added triethylamine (52.4 mmol, 7.3 mL) and then benzyloxycarbonyl chloride (42 mmol, 5.93 mL) dropwise . The suspension was stirred at room temperature for 24 hours and the precipitated solid was filtered. The organic solution was evaporated under vacuum to give an oily residue which was chromatographed on silica gel eluting with ethyl ether and petroleum ether mixture to afford 8-benzyloxycarbonyl 1,4-dioxa-8- azaspiro [4,5] decane in quantitative yield. 1 H-NMR (CDCl3): 1.63 (m, 4H); 3.56 (m,4H); 3.89 (s, 4H); 5.09 (s, 2H); 7.28 (s, 5H). The suspension was stirred at room temperature for 24 hours the precipitated solid was filtered The organic solution was evaporated under vacuum to give an oily residue which was chromatographed on silica gel eluting with ethyl ether and petroleum ether mixture

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

実験手順: To a well-stirred and ice-cooled solution of 1,4-dioxa-8-azaspiro[4,5]decane (34.9 mmol, 5 g) in dichloromethane (200 mL) under an argon atmosphere, is added triethylamine (52.4 mmol, 7.3 mL) and then benzyloxycarbonyl chloride (42 mmol, 5.93 mL) dropwise . The suspension was stirred at room temperature for 24 hours and the precipitated solid was filtered. The organic solution was evaporated under vacuum to give an oily residue which was chromatographed on silica gel eluting with ethyl ether and petroleum ether mixture to afford 8-benzyloxycarbonyl 1,4-dioxa-8- azaspiro [4,5] decane in quantitative yield. 1 H-NMR (CDCl3): 1.63 (m, 4H); 3.56 (m,4H); 3.89 (s, 4H); 5.09 (s, 2H); 7.28 (s, 5H). The suspension was stirred at room temperature for 24 hours the precipitated solid was filtered The organic solution was evaporated under vacuum to give an oily residue which was chromatographed on silica gel eluting with ethyl ether and petroleum ether mixture

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

実験手順: To a stirred solution 8-benzyloxycarbonyl 1,4-dioxa-8-azaspiro[4,5]decane (0.037 mol, 10 g) in tetrahydrofuran (150 mL) was added a solution of hydrochloric acid 5% (20 mL) dropwise a room temperature. The solution was stirred for 18 h (TLC control) and then evaporated under vacuum to small volume (20 mL) and neutralized with saturated sodium bicarbonate solution. The aqueous solution was extracted with ethyl acetate (3×100 mL) and the organic layers were dried on sodium sulfate and finally evaporated under vacuum to give 1-benzyloxycarbonyl piperidin4-one practically pure which was then used in the next step without any further purification (92% yield). 1H-NMR (CDCl3): 1.63 (m, 4H); 3.56 (m,4H); 5.09 (s, 2H); 7.28 (s, 5H). evaporated under vacuum to small volume (20 mL) The aqueous solution was extracted with ethyl acetate (3×100 mL) the organic layers were dried on sodium sulfate finally evaporated under vacuum

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

実験手順: To a stirred solution 8-benzyloxycarbonyl 1,4-dioxa-8-azaspiro[4,5]decane (0.037 mol, 10 g) in tetrahydrofuran (150 mL) was added a solution of hydrochloric acid 5% (20 mL) dropwise a room temperature. The solution was stirred for 18 h (TLC control) and then evaporated under vacuum to small volume (20 mL) and neutralized with saturated sodium bicarbonate solution. The aqueous solution was extracted with ethyl acetate (3×100 mL) and the organic layers were dried on sodium sulfate and finally evaporated under vacuum to give 1-benzyloxycarbonyl piperidin4-one practically pure which was then used in the next step without any further purification (92% yield). 1H-NMR (CDCl3): 1.63 (m, 4H); 3.56 (m,4H); 5.09 (s, 2H); 7.28 (s, 5H). evaporated under vacuum to small volume (20 mL) The aqueous solution was extracted with ethyl acetate (3×100 mL) the organic layers were dried on sodium sulfate finally evaporated under vacuum

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

実験手順: To a well-stirred and ice-cooled solution of 1,4-dioxa-8-azaspiro[4,5]decane (34.9 mmol, 5 g) in dichloromethane (200 mL) under an argon atmosphere, is added triethylamine (52.4 mmol, 7.3 mL) and then benzyloxycarbonyl chloride (42 mmol, 5.93 mL) dropwise. The suspension was stirred at room temperature for 24 hours and the precipitated solid was filtered. The organic solution was evaporated under vacuum to give an oily residue which was chromatographed on silica gel eluting with ethyl ether and petroleum ether mixture to afford 8-benzyloxycarbonyl 1,4-dioxa-8-azaspiro [4,5] decane in quantitative yield. 1H-NMR (CDCl3): 1.63 (m, 4H); 3.56 (m,4H); 3.89 (s, 4H); 5.09 (s, 2H); 7.28 (s, 5H). The suspension was stirred at room temperature for 24 hours the precipitated solid was filtered The organic solution was evaporated under vacuum to give an oily residue which was chromatographed on silica gel eluting with ethyl ether and petroleum ether mixture

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

実験手順: To a stirred solution of 8-benzyloxycarbonyl 1,4-dioxa-8-azaspiro[4,5] decane (0.037 mol, 10 g) in tetrahydrofuran (150 mL) was added a solution of hydrochloric acid 5% (20 mL) dropwise at room temperature. The solution was stirred for 18 h (TLC control) and then evaporated under vacuum to small volume (20 mL) and neutralized with a saturated sodium bicarbonate solution. The aqueous solution was extracted with ethyl acetate (3×100 mL) and the organic layers were dried over sodium sulfate and finally evaporated under vacuum to give 1-benzyloxycarbonyl piperidin-4-one which was substantially pure and which was used in the next step without any purification (92% yield). 1H-NMR (CDCl3): 1.63 (m, 4H); 3.56 (m,4H); 5.09 (s, 2H); 7.28 (s, 5H). evaporated under vacuum to small volume (20 mL) The aqueous solution was extracted with ethyl acetate (3×100 mL) the organic layers were dried over sodium sulfate finally evaporated under vacuum

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

実験手順: To a well-stirred and ice-cooled solution of 1,4-dioxa-8-azaspiro[4.5]decane (34.9 mmol, 5 g) in dichloromethane (200 mL) under an argon atmosphere, was added triethylamine (52.4 mmol, 7.3 mL) and then benzyloxycarbonyl chloride (42 mmol, 5.93 mL) dropwise. The suspension was stirred at room temperature for 24 hours and the precipitated solid was filtered. The organic solution was evaporated under vacuum to give an oily residue which was chromatographed on silica gel eluting with a mixture of ethyl ether and petroleum ether to afford 8-benzyloxycarbonyl 1,4-dioxa-8-azaspiro [4,5] decane in quantitative yield. 1H-NMR (CDCl3): 1.63 (m, 4H); 3.56 (m,4H); 3.89 (s, 4H); 5.09 (s, 2H); 7.28 (s, 5H). The suspension was stirred at room temperature for 24 hours the precipitated solid was filtered The organic solution was evaporated under vacuum to give an oily residue which was chromatographed on silica gel eluting with a mixture of ethyl ether and petroleum ether

反応条件: temp:0.00; pressure:0.00; stir:

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: To a stirred solution 8-benzyloxycarbonyl 1,4-dioxa-8-azaspiro[4,5]decane (0.037 mol, 10 g) in tetrahydrofuran (150 mL) was added a solution of hydrochloric acid 5% (20 mL) dropwise a room temperature. The solution was stirred for 18 h (TLC control) and then evaporated under vacuum to small volume (20 mL) and neutralized with saturated sodium bicarbonate solution. The aqueous solution was extracted with ethyl acetate (3×100 mL) and the organic layers were dried on sodium sulfate and finally evaporated under vacuum to give 1-benzyloxycarbonyl piperidin-4-one practically pure which was then used in the next step without any further purification (92% yield). evaporated under vacuum to small volume (20 mL) The aqueous solution was extracted with ethyl acetate (3×100 mL) the organic layers were dried on sodium sulfate finally evaporated under vacuum