No renderable structure data available
C1CN(CCC12OCCO2)C(=O)OCC3=CC=CC=C3Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | benzyl 1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylate |
|---|---|
| IUPAC Name | — |
| CAS Number | 139524-58-6 |
| Database ID | 15165038 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
benzyl 1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylate (CAS 139524-58-6) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 15165038
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-de28354b07b04efdadfe7c1a34051d89Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-42be61aac9de438fa0713a6c066a97a2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-d7a6e5edbe684cfd8f7886d49fafc366Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-d7a6e5edbe684cfd8f7886d49fafc366Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-647b743ab1e64873a444a3ec166d5dabConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-647b743ab1e64873a444a3ec166d5dabConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-23d0d9452f6b4b6fad3c9ef05fefc40dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-bf439982f7684991b0e5d3899a0ff9a5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-6466b58dd67b434d9a80846a2319868dConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-de28354b07b04efdadfe7c1a34051d89Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-42be61aac9de438fa0713a6c066a97a2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-539f11f2e7a946dabfe112ff0291cca4PubChem References
These sources are listed in the compound's public database record.
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