No renderable structure data available
CC(C)(C)OC(=O)NCC1CCC(=O)CC1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | tert-butyl N-[(4-oxocyclohexyl)methyl]carbamate |
|---|---|
| IUPAC Name | — |
| CAS Number | 809273-70-9 |
| Database ID | 40424027 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
tert-butyl N-[(4-oxocyclohexyl)methyl]carbamate (CAS 809273-70-9) 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 40424027
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-a17820c6aa4242ca96cc458f9e8f0147Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f6050f91dffa44b4b4d9302ffe094483Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a vigorous stirring solution of tert-butyl (4-oxocyclohexyl)methylcarbamate (1.7 g) in tetrahydrofuran (40 mL) at −78° C. was dropwise added 1.6 M methyllithium (14.02 mL) in ether. After completion of the addition, the mixture was stirred at −78° C. for 1.2 hours and poured into a cold aqueous NH4Cl solution. The resulting mixture was extracted with dichloromethane (3×100 mL) and the organic layer was dried over Na2SO4, filtered and concentrated. The residue was dissolved in dichloromethane and loaded onto an Analogix purification system, eluted with 0-50% ethyl acetate in dichloromethane to provide the title compound. at −78° C. After completion of the addition The resulting mixture was extracted with dichloromethane (3×100 mL) the organic layer was dried over Na2SO4 filtered concentrated The residue was dissolved in dichloromethane loaded onto an Analogix purification system eluted with 0-50% ethyl acetate in dichloromethane
Source ID: ord-27b2f76d08684fa1af69f03b8afd815dConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of tert-butyl (4-oxocyclohexyl)methylcarbamate (1.00 g) was dissolved in tetrahydrofuran (20 mL) and cooled to −78° C. Methylmagnesium bromide (4.40 mL) was added dropwise. The reaction was stirred for 2 hours at −78° C. then allowed to warm to 0° C. and stirred for 30 minutes. The resulting suspension was quenched with water (10 mL), diluted with ether (50 mL), washed with ammonium chloride (25 mL), washed with brine (25 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 80 g) eluting using a gradient of 5% to 50% ethyl acetate/dichloromethane over 30 minutes (flow=60 mL/min) gave the title compound as a ˜2:1 mixture of cis and trans isomers. to warm to 0° C. stirred for 30 minutes The resulting suspension was quenched with water (10 mL) diluted with ether (50 mL) washed with ammonium chloride (25 mL) washed with brine (25 mL) dried over magnesium sulfate filtered concentrated Silica gel chromatography (Reveleris 80 g) eluting over 30 minutes
Source ID: ord-ee4a7173193f4b428d87a564b3797540Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a vigorous stirring solution of tert-butyl (4-oxocyclohexyl)methylcarbamate (1.7 g) in tetrahydrofuran (40 mL) at −78° C. was dropwise added 1.6 M methyllithium (14.02 mL) in ether. After completion of the addition, the mixture was stirred at −78° C. for 1.2 hours and poured into a cold NH4Cl aqueous solution. The resulting mixture was extracted with dichloromethane (100 ml, three times) and the organic layer was dried over Na2SO4, filtered, and concentrated. The residue was dissolved in dichloromethane and loaded onto an Analogix purification system, and it was eluted with 0-50% ethyl acetate in dichloromethane to provide the title compound. at −78° C. After completion of the addition The resulting mixture was extracted with dichloromethane (100 ml, three times) the organic layer was dried over Na2SO4 filtered concentrated The residue was dissolved in dichloromethane loaded onto an Analogix purification system, and it was eluted with 0-50% ethyl acetate in dichloromethane
Source ID: ord-e188b430c9bd47828bdb6d86f85d19eaConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a vigorous stirring solution of tert-butyl (4-oxocyclohexyl)methylcarbamate (1.7 g) in tetrahydrofuran (40 mL) at −78° C. was dropwise added 1.6 M methyllithium (14.02 mL) in ether. After completion of the addition, the mixture was stirred at −78° C. for 1.2 hours and poured into a cold NH4Cl aqueous solution. The resulting mixture was extracted with dichloromethane (100 ml, three times) and the organic layer was dried over Na2SO4, filtered, and concentrated. The residue was dissolved in dichloromethane and loaded onto an Analogix purification system, and it was eluted with 0-50% ethyl acetate in dichloromethane to provide the title compound. at −78° C. After completion of the addition The resulting mixture was extracted with dichloromethane (100 ml, three times) the organic layer was dried over Na2SO4 filtered concentrated The residue was dissolved in dichloromethane loaded onto an Analogix purification system, and it was eluted with 0-50% ethyl acetate in dichloromethane
Source ID: ord-4c0e9158a1f74c60ae42e11b4248446aConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a vigorous stirring solution of tert-butyl (4-oxocyclohexyl)methylcarbamate (1.7 g) in tetrahydrofuran (40 mL) at −78° C. was dropwise added 1.6 M methyllithium (14.02 mL) in ether. After completion of the addition, the mixture was stirred at −78° C. for 1.2 hours and poured into a cold NH4Cl aqueous solution. The resulting mixture was extracted with dichloromethane (100 ml, three times) and the organic layer was dried over Na2SO4, filtered, and concentrated. The residue was dissolved in dichloromethane and loaded onto an Analogix purification system, and it was eluted with 0-50% ethyl acetate in dichloromethane to provide the title compound. at −78° C. After completion of the addition The resulting mixture was extracted with dichloromethane (100 ml, three times) the organic layer was dried over Na2SO4 filtered concentrated The residue was dissolved in dichloromethane loaded onto an Analogix purification system, and it was eluted with 0-50% ethyl acetate in dichloromethane
Source ID: ord-4c0e9158a1f74c60ae42e11b4248446aConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of tert-butyl(4-oxocyclohexyl)methylcarbamate (1.00 g) was dissolved in tetrahydrofuran (20 mL) and cooled to −78° C. Methylmagnesium bromide (4.40 mL) was added dropwise. The reaction was stirred for 2 hours at −78° C. then allowed to warm to 0° C. and stirred for 30 minutes. The resulting suspension was quenched with water (10 mL), diluted with ether (50 mL), washed with ammonium chloride (25 mL), washed with brine (25 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 80 g) eluting using a gradient of 5% to 50% ethyl acetate/dichloromethane over 30 minutes (flow=60 mL/min) gave the title compound as a 2:1 mixture of cis and trans isomers. to warm to 0° C. stirred for 30 minutes The resulting suspension was quenched with water (10 mL) diluted with ether (50 mL) washed with ammonium chloride (25 mL) washed with brine (25 mL) dried over magnesium sulfate filtered concentrated Silica gel chromatography (Reveleris 80 g) eluting over 30 minutes
Source ID: ord-9895707da33945b2a94b35b15629b01cConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a vigorous stirring solution of tert-butyl(4-oxocyclohexyl)methylcarbamate (1.7 g) in tetrahydrofuran (40 mL) at −78° C. was dropwise added 1.6 M methyllithium (14.02 mL) in ether. After completion of the addition, the mixture was stirred at −78° C. for 1.2 hours and poured into a cold NH4Cl aqueous solution. The resulting mixture was extracted with dichloromethane (100 ml, three times) and the organic layer was dried over Na2SO4, filtered, and concentrated. The residue was dissolved in dichloromethane and loaded onto an Analogix purification system, and it was eluted with 0-50% ethyl acetate in dichloromethane to provide the title compound. at −78° C. After completion of the addition The resulting mixture was extracted with dichloromethane (100 ml, three times) the organic layer was dried over Na2SO4 filtered concentrated The residue was dissolved in dichloromethane loaded onto an Analogix purification system, and it was eluted with 0-50% ethyl acetate in dichloromethane
Source ID: ord-13b474741b6b49c9b5f4191f2d9d8e68Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a vigorous stirring solution of tert-butyl(4-oxocyclohexyl)methylcarbamate (1.7 g) in tetrahydrofuran (40 mL) at −78° C. was dropwise added 1.6 M methyllithium (14.02 mL) in ether. After completion of the addition, the mixture was stirred at −78° C. for 1.2 hours and poured into a cold NH4Cl aqueous solution. The resulting mixture was extracted with dichloromethane (100 ml, three times) and the organic layer was dried over Na2SO4, filtered, and concentrated. The residue was dissolved in dichloromethane and loaded onto an Analogix purification system, and it was eluted with 0-50% ethyl acetate in dichloromethane to provide the title compound. at −78° C. After completion of the addition The resulting mixture was extracted with dichloromethane (100 ml, three times) the organic layer was dried over Na2SO4 filtered concentrated The residue was dissolved in dichloromethane loaded onto an Analogix purification system, and it was eluted with 0-50% ethyl acetate in dichloromethane
Source ID: ord-9f5eaf8db62c4d8a8a885afcb591638fConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a vigorous stirring solution of tert-butyl(4-oxocyclohexyl)methylcarbamate (1.7 g) in tetrahydrofuran (40 mL) at −78° C. was dropwise added 1.6 M methyllithium (14.02 mL) in ether. After completion of the addition, the mixture was stirred at −78° C. for 1.2 hours and poured into a cold NH4Cl aqueous solution. The resulting mixture was extracted with dichloromethane (100 ml, three times) and the organic layer was dried over Na2SO4, filtered, and concentrated. The residue was dissolved in dichloromethane and loaded onto an Analogix purification system, and it was eluted with 0-50% ethyl acetate in dichloromethane to provide the title compound. at −78° C. After completion of the addition The resulting mixture was extracted with dichloromethane (100 ml, three times) the organic layer was dried over Na2SO4 filtered concentrated The residue was dissolved in dichloromethane loaded onto an Analogix purification system, and it was eluted with 0-50% ethyl acetate in dichloromethane
Source ID: ord-9f5eaf8db62c4d8a8a885afcb591638fConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of tert-butyl (4-oxocyclohexyl)methylcarbamate (1.00 g) was dissolved in tetrahydrofuran (20 mL) and cooled to −78° C. Methylmagnesium bromide (4.40 mL) was added dropwise. The reaction was stirred for 2 hours at −78° C. then allowed to warm to 0° C. and stirred for 30 minutes. The resulting suspension was quenched with water (10 mL), diluted with ether (50 mL), washed with ammonium chloride (25 mL), washed with brine (25 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 80 g) eluting using a gradient of 5% to 50% ethyl acetate/dichloromethane over 30 minutes (flow=60 mL/min) gave the title compound as a 2:1 mixture of cis and trans isomers. to warm to 0° C. stirred for 30 minutes The resulting suspension was quenched with water (10 mL) diluted with ether (50 mL) washed with ammonium chloride (25 mL) washed with brine (25 mL) dried over magnesium sulfate filtered concentrated Silica gel chromatography (Reveleris 80 g) eluting over 30 minutes
Source ID: ord-16888053314f47c886ed1e8fa8056986PubChem References
These sources are listed in the compound's public database record.
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