No renderable structure data available
O=C1C2(CCN(C(OC(C)(C)C)=O)CC2)CCC1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | tert-butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate |
|---|---|
| IUPAC Name | — |
| CAS Number | 191805-29-5 |
| Database ID | 10848487 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
tert-butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate (CAS 191805-29-5) 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 10848487
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-c3d2c832fe43485abcdd85ffd30345ecConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Procedure 1, Step G (0.526 g, 2.08 mmol) was dried by evaporating with toluene (10 mL) three times in vacuo, dissolved in methyl-tert-butyl ether (5 mL), and cooled to −78° C. To this solution was added ethyl formate (0.336 mL, 4.15 mmol) and then potassium t-butoxide (0.466 g, 4.16 mmol). After 2 days, the reaction mixture was diluted with diethyl ether, poured into 2N HCl, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 0.575 g. The residue was purified by flash chromatography eluting with 45% ethyl acetate/hexanes to give the title compound (0.303 g). MS/EI (acetonitrile/water): m/z 304 (M+1+Na) retention time=2.9 min. by evaporating with toluene (10 mL) three times in vacuo dissolved in methyl-tert-butyl ether (5 mL) extracted three times with diethyl ether washed with brine dried over sodium sulfate filtered concentrated to afford 0.575 g The residue was purified by flash chromatography eluting with 45% ethyl acetate/hexanes
Source ID: ord-01aabc2e796f428ba758c5068521a6d6Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Procedure 1, Step G (1.2 g, 4.70 mmol) was dried by evaporating with toluene (5 mL) three times in vacuo, dissolved in tetrahydrofuran (50 mL), and cooled to −78° C. To this solution was added lithium diisopropylamide mono(tetrahydrofuran) (6.3 mL, 9.4 mmol, 1.5 M in cyclohexane). The reaction mixture was stirred for 35 min at −78° C. before adding acetaldehyde (0.527 mL, 9.4 mmol). After 10 min, the reaction mixture was diluted with diethyl ether, poured into saturated ammonium chloride, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 6.7 g of a clear oil. The residue was purified by flash chromatography eluting with 20–40% ethyl acetate/hexanes to give the title compound (0.620 g). by evaporating with toluene (5 mL) three times in vacuo dissolved in tetrahydrofuran (50 mL) After 10 min extracted three times with diethyl ether washed with brine dried over sodium sulfate filtered concentrated
Source ID: ord-0c06c86d3f3444378259f57ae88f4d91Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Step G (4.5 g, 17.8 mmol) was dried by evaporating with toluene (10 mL) three times in vacuo, dissolved in tetrahydrofuran (100 mL), and cooled to −78° C. To this solution was added lithium diisopropylamide mono(tetrahydrofuran) (24 mL, 36 mmol, 1.5 M in cyclohexane). The reaction mixture was stirred for 30 min at −78° C. before adding propionaldehyde (2.6 mL, 36 mmol). After 5 min, the reaction mixture was diluted with diethyl ether, poured into saturated ammonium chloride, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 6.7 g of a clear oil. The residue was purified by flash chromatography eluting with 20–30% ethyl acetate in hexanes to give the title compound (4.75 g). by evaporating with toluene (10 mL) three times in vacuo dissolved in tetrahydrofuran (100 mL) After 5 min extracted three times with diethyl ether washed with brine dried over sodium sulfate filtered concentrated
Source ID: ord-f4d34c0f487347f9a801ff3387bd1e3dConditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of tert-butyl 2-(methoxycarbonyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate (17.2 g, 0.055 mol) from Step F in a 2:2:1 mixture of ethanol/tetrahydrofuran/water (555 mL) was added pulverized lithium hydroxide (26 g, 1.10 mol). The reaction mixture was heated to 90° C. for 60 h. The reaction mixture was allowed to cool and was then concentrated, dissolved in water and dichloromethane, and extracted three times with dichloromethane. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 11.4 g. The residue was purified by flash chromatography eluting with 20–30% ethyl acetate in hexanes to give the title compound (9.41 g). was added to cool was then concentrated dissolved in water dichloromethane, and extracted three times with dichloromethane washed with brine dried over sodium sulfate filtered concentrated to afford 11.4 g The residue was purified by flash chromatography eluting with 20–30% ethyl acetate in hexanes
Source ID: ord-279bb325608143949a9c5045f8750794Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c3d2c832fe43485abcdd85ffd30345ecConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Procedure 1, Step G (0.526 g, 2.08 mmol) was dried by evaporating with toluene (10 mL) three times in vacuo, dissolved in methyl-tert-butyl ether (5 mL), and cooled to −78° C. To this solution was added ethyl formate (0.336 mL, 4.15 mmol) and then potassium t-butoxide (0.466 g, 4.16 mmol). After 2 days, the reaction mixture was diluted with diethyl ether, poured into 2N HCl, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 0.575 g. The residue was purified by flash chromatography eluting with 45% ethyl acetate/hexanes to give the title compound (0.303 g). MS/EI (acetonitrile/water): m/z 304 (M+1+Na) retention time=2.9 min. by evaporating with toluene (10 mL) three times in vacuo dissolved in methyl-tert-butyl ether (5 mL) extracted three times with diethyl ether washed with brine dried over sodium sulfate filtered concentrated to afford 0.575 g The residue was purified by flash chromatography eluting with 45% ethyl acetate/hexanes
Source ID: ord-01aabc2e796f428ba758c5068521a6d6Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Procedure 1, Step G (1.2 g, 4.70 mmol) was dried by evaporating with toluene (5 mL) three times in vacuo, dissolved in tetrahydrofuran (50 mL), and cooled to −78° C. To this solution was added lithium diisopropylamide mono(tetrahydrofuran) (6.3 mL, 9.4 mmol, 1.5 M in cyclohexane). The reaction mixture was stirred for 35 min at −78° C. before adding acetaldehyde (0.527 mL, 9.4 mmol). After 10 min, the reaction mixture was diluted with diethyl ether, poured into saturated ammonium chloride, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 6.7 g of a clear oil. The residue was purified by flash chromatography eluting with 20–40% ethyl acetate/hexanes to give the title compound (0.620 g). by evaporating with toluene (5 mL) three times in vacuo dissolved in tetrahydrofuran (50 mL) After 10 min extracted three times with diethyl ether washed with brine dried over sodium sulfate filtered concentrated
Source ID: ord-0c06c86d3f3444378259f57ae88f4d91Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Step G (4.5 g, 17.8 mmol) was dried by evaporating with toluene (10 mL) three times in vacuo, dissolved in tetrahydrofuran (100 mL), and cooled to −78° C. To this solution was added lithium diisopropylamide mono(tetrahydrofuran) (24 mL, 36 mmol, 1.5 M in cyclohexane). The reaction mixture was stirred for 30 min at −78° C. before adding propionaldehyde (2.6 mL, 36 mmol). After 5 min, the reaction mixture was diluted with diethyl ether, poured into saturated ammonium chloride, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 6.7 g of a clear oil. The residue was purified by flash chromatography eluting with 20–30% ethyl acetate in hexanes to give the title compound (4.75 g). by evaporating with toluene (10 mL) three times in vacuo dissolved in tetrahydrofuran (100 mL) After 5 min extracted three times with diethyl ether washed with brine dried over sodium sulfate filtered concentrated
Source ID: ord-f4d34c0f487347f9a801ff3387bd1e3dConditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of tert-butyl 2-(methoxycarbonyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate (17.2 g, 0.055 mol) from Step F in a 2:2:1 mixture of ethanol/tetrahydrofuran/water (555 mL) was added pulverized lithium hydroxide (26 g, 1.10 mol). The reaction mixture was heated to 90° C. for 60 h. The reaction mixture was allowed to cool and was then concentrated, dissolved in water and dichloromethane, and extracted three times with dichloromethane. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 11.4 g. The residue was purified by flash chromatography eluting with 20–30% ethyl acetate in hexanes to give the title compound (9.41 g). was added to cool was then concentrated dissolved in water dichloromethane, and extracted three times with dichloromethane washed with brine dried over sodium sulfate filtered concentrated to afford 11.4 g The residue was purified by flash chromatography eluting with 20–30% ethyl acetate in hexanes
Source ID: ord-279bb325608143949a9c5045f8750794Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Procedure 1, Step G (0.526 g, 2.08 mmol) was dried by evaporating with toluene (10 mL) three times in vacuo, dissolved in methyl-tert-butyl ether (5 mL), and cooled to −78° C. To this solution was added ethyl formate (0.336 mL, 4.15 mmol) and then potassium t-butoxide (0.466 g, 4.16 mmol). After 2 days, the reaction mixture was diluted with diethyl ether, poured into 2N HCl, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 0.575 g. The residue was purified by flash chromatography eluting with 45% ethyl acetate/hexanes to give the title compound (0.303 g). MS/EI (acetonitrile/water): m/z 304 (M+1+Na) retention time=2.9 min. by evaporating with toluene (10 mL) three times in vacuo dissolved in methyl-tert-butyl ether (5 mL) extracted three times with diethyl ether washed with brine dried over sodium sulfate filtered concentrated to afford 0.575 g The residue was purified by flash chromatography eluting with 45% ethyl acetate/hexanes
Source ID: ord-01aabc2e796f428ba758c5068521a6d6Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Procedure 1, Step G (1.2 g, 4.70 mmol) was dried by evaporating with toluene (5 mL) three times in vacuo, dissolved in tetrahydrofuran (50 mL), and cooled to −78° C. To this solution was added lithium diisopropylamide mono(tetrahydrofuran) (6.3 mL, 9.4 mmol, 1.5 M in cyclohexane). The reaction mixture was stirred for 35 min at −78° C. before adding acetaldehyde (0.527 mL, 9.4 mmol). After 10 min, the reaction mixture was diluted with diethyl ether, poured into saturated ammonium chloride, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 6.7 g of a clear oil. The residue was purified by flash chromatography eluting with 20–40% ethyl acetate/hexanes to give the title compound (0.620 g). by evaporating with toluene (5 mL) three times in vacuo dissolved in tetrahydrofuran (50 mL) After 10 min extracted three times with diethyl ether washed with brine dried over sodium sulfate filtered concentrated
Source ID: ord-0c06c86d3f3444378259f57ae88f4d91PubChem References
These sources are listed in the compound's public database record.
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