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CC(C)(C)OC(=O)NC(C#N)C1=CC=CC=C1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | tert-butyl N-[cyano(phenyl)methyl]carbamate |
|---|---|
| IUPAC Name | — |
| CAS Number | 78558-73-3 |
| Database ID | 4231037 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
tert-butyl N-[cyano(phenyl)methyl]carbamate (CAS 78558-73-3) 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 4231037
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-9dcf9f4017ab4fb1a7100629b20b838aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-76ada8aaab534d0a9d95687698c39f4cConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-573d510fd7d44b3cafbb1a2de36fa105Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an ice cooled solution of 3.69 g of 4-amino-3,3-dimethyl-1-[1-(R)-phenylethyl]-pyrrolidine in 40 ml of anhydrous tetrahydrofuran there was added 4.92 g of 2-(tert-butoxycarbonylamino)-2-phenylacetonitrile and the mixture was stirred at room temperature for 1 hr. Solvent was removed under reduced pressure, and to the residue there was added ethyl acetate. The mixture was washed with a 1N sodium hydroxide aqueous solution three times and then dried. Solvent was then removed under reduced pressure. The residue was purified through column chromatography using 200 g of silica gel in a column with chloroform as the eluant containing from 1% to 5% methanol to yield 4.32 g of the titled compound. Solvent was removed under reduced pressure to the residue there was added ethyl acetate The mixture was washed with a 1N sodium hydroxide aqueous solution three times dried Solvent was then removed under reduced pressure The residue was purified through column chromatography containing from 1% to 5% methanol
Source ID: ord-7d1a51f95975424bb5439f6ffd32e473Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an ice-cooled solution of 2.9 g of 8-amino-6-[1-(R)-phenylethyl]-6-azaspiro[3.4]octane in 30 ml of tetrahydrofuran there was added 3.3 g of 2-(tert-butoxycarbonyl-amino)-2-phenylacetonitrile and the resulting mixture was stirred at room temperature for 30 min. The solvent was removed under reduced pressure, and ethyl acetate was added to the resulting residue. The mixture was washed with a 1N sodium hydroxide aqueous solution three times and then dried. The solvent was removed under reduced pressure and the resulting residue was purified by column chromatography using 50 g of silica gel. The column was eluted with chloroform, chloroform containing methanol and 4.1 g of the titled compound was obtained from a eluate when the eluant was chloroform containing 1% (v/v) of methanol. The solvent was removed under reduced pressure, and ethyl acetate was added to the resulting residue The mixture was washed with a 1N sodium hydroxide aqueous solution three times dried The solvent was removed under reduced pressure the resulting residue was purified by column chromatography The column was eluted with chloroform, chloroform containing methanol
Source ID: ord-d1ab5fb142a845ea85d6339642921aa8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an ice cooled solution of 3.69 g of 4-amino-3,3-dimethyl-1-[1-(R)-phenylethyl]-pyrrolidine in 40 ml of anhydrous tetrahydrofuran there was added 4.92 g of 2-(tert-butoxycarbonylamino)-2-phenylacetonitrile and the mixture was stirred at room temperature for 1 hr. Solvent was removed under reduced pressure, and to the residue there was added ethyl acetate. The mixture was washed with a 1N sodium hydroxide aqueous solution three times and then dried. Solvent was then removed under reduced pressure. The residue was purified through column chromatography using 200 g of silica gel in a column with chloroform as the eluant containing from 1% to 5% methanol to yield 4.32 g of the titled compound. Solvent was removed under reduced pressure to the residue there was added ethyl acetate The mixture was washed with a 1N sodium hydroxide aqueous solution three times dried Solvent was then removed under reduced pressure The residue was purified through column chromatography containing from 1% to 5% methanol
Source ID: ord-ce058878bf2246e8bd4d92854c86e262Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an ice-cooled solution of 2.9 g of 8-amino-6-[1-(R)-phenylethyl]-6-azaspiro[3.4]octane in 30 ml of tetrahydrofuran there was added 3.3 g of 2-(tertbutoxycarbonyl-amino)-2-phenylacetonitrile and the resulting mixture was stirred at room temperature for 30 min. The solvent was removed under reduced pressure, and ethyl acetate was added to the resulting residue. The mixture was washed with a 1N sodium hydroxide aqueous solution three times and then dried. The solvent was removed under reduced pressure and the resulting residue was purified by column chromatography using 50 g of silica gel. The column was eluted with chloroform, chloroform containing methanol and 4.1 g of the titled compound was obtained from a eluate when the eluant was chloroform containing 1% (v/v) of methanol. The solvent was removed under reduced pressure, and ethyl acetate was added to the resulting residue The mixture was washed with a 1N sodium hydroxide aqueous solution three times dried The solvent was removed under reduced pressure the resulting residue was purified by column chromatography The column was eluted with chloroform, chloroform containing methanol
Source ID: ord-c0633b8313214ab682affe5e81ed4befConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an ice cooled solution of 3.69 g of 4-amino-3,3-dimethyl-1-[1-(R)-phenylethyl]-pyrrolidine in 40 ml of anhydrous tetrahydrofuran there was added 4.92 g of 2-(tert-butoxycarbonylamino)-2-phenylacetonitrile and the mixture was stirred at room temperature for 1 hr. Solvent was removed under reduced pressure, and to the residue there was added ethyl acetate. The mixture was washed with a 1N sodium hydroxide aqueous solution three times and then dried. Solvent wa then removed under reduced pressure. The residue was purified through column chromatography using 200 g of silica gel in a column with chloroform as the eluant containing from 1% to 5% methanol to yield 4.32 g of the titled compound. 1H-NMR(CDCl3) δ ppm;1.00, 16(each 3H, s), 1.40(3H, d, J=7.2 Hz), 1.52(9H, s), 2.00-3.62(5H, m), 3.85-4.10(1H, m), 4.90(1H, bs), 7.38(5H, s) Solvent was removed under reduced pressure to the residue there was added ethyl acetate The mixture was washed with a 1N sodium hydroxide aqueous solution three times dried Solvent wa then removed under reduced pressure The residue was purified through column chromatography containing from 1% to 5% methanol
Source ID: ord-5534424320a84165b36668a2812432e5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an ice cooled solution of 3.69 g of 4-amino-3,3-dimethyl-1-[1-(R)-phenylethyl]-pyrrolidine in 40 ml of anhydrous tetrahydrofuran there was added 4.92 g of 2-(tert-butoxycarbonylamino)-2-phenylacetonitrile and the mixture was stirred at room temperature for 1 hr. Solvent was removed under reduced pressure, and to the residue there was added ethyl acetate. The mixture was washed with a 1N sodium hydroxide aqueous solution three times and then dried. Solvent wa then removed under reduced pressure. The residue was purified through column chromatography using 200 g of silica gel in a column with chloroform as the eluant containing from 1% to 5% methanol to yield 4.32 g of the titled compound. 1H-NMR(CDCl3) δ ppm;1.00, 16(each 3H, s), 1.40(3H, d, J=7.2 Hz), 1.52(9H, s), 2.00-3.62(5H, m), 3.85-4.10(1H, m), 4.90(1H, bs), 7.38(5H, s) Solvent was removed under reduced pressure to the residue there was added ethyl acetate The mixture was washed with a 1N sodium hydroxide aqueous solution three times dried Solvent wa then removed under reduced pressure The residue was purified through column chromatography containing from 1% to 5% methanol
Source ID: ord-5534424320a84165b36668a2812432e5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an ice cooled solution of 3.69 g of 4-amino-3,3-dimethyl-1-[1-(R)-phenylethyl]-pyrrolidine in 40 ml of anhydrous tetrahydrofuran there was added 4.92 g of 2-(tert-butoxycarbonylamino)-2-phenylacetonitrile and the mixture was stirred at room temperature for 1 hr. Solvent was removed under reduced pressure, and to the residue there was added ethyl acetate. The mixture was washed with a 1N sodium hydroxide aqueous solution three times and then dried. Solvent was then removed under reduced pressure. The residue was purified through column chromatography using 200 g of silica gel in a column with chloroform as the eluant containing from 1% to 5% methanol to yield 4.32 g of the titled compound. Solvent was removed under reduced pressure to the residue there was added ethyl acetate The mixture was washed with a 1N sodium hydroxide aqueous solution three times dried Solvent was then removed under reduced pressure The residue was purified through column chromatography containing from 1% to 5% methanol
Source ID: ord-7d1a51f95975424bb5439f6ffd32e473Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an ice cooled solution of 3.69 g of 4-amino-3,3-dimethyl-1-[1-(R)-phenylethyl]-pyrrolidine in 40 ml of anhydrous tetrahydrofuran there was added 4.92 g of 2-(tert-butoxycarbonylamino)-2-phenylacetonitrile and the mixture was stirred at room temperature for 1 hr. Solvent was removed under reduced pressure, and to the residue there was added ethyl acetate. The mixture was washed with a 1N sodium hydroxide aqueous solution three times and then dried. Solvent was then removed under reduced pressure. The residue was purified through column chromatography using 200 g of silica gel in a column with chloroform as the eluant containing from 1% to 5% methanol to yield 4.32 g of the titled compound. Solvent was removed under reduced pressure to the residue there was added ethyl acetate The mixture was washed with a 1N sodium hydroxide aqueous solution three times dried Solvent was then removed under reduced pressure The residue was purified through column chromatography containing from 1% to 5% methanol
Source ID: ord-7d1a51f95975424bb5439f6ffd32e473Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an ice-cooled solution of 2.9 g of 8-amino-6-[1-(R)-phenylethyl]-6-azaspiro[3.4]octane in 30 ml of tetrahydrofuran there was added 3.3 g of 2-(tert-butoxycarbonyl-amino)-2-phenylacetonitrile and the resulting mixture was stirred at room temperature for 30 min. The solvent was removed under reduced pressure, and ethyl acetate was added to the resulting residue. The mixture was washed with a 1N sodium hydroxide aqueous solution three times and then dried. The solvent was removed under reduced pressure and the resulting residue was purified by column chromatography using 50 g of silica gel. The column was eluted with chloroform, chloroform containing methanol and 4.1 g of the titled compound was obtained from a eluate when the eluant was chloroform containing 1% (v/v) of methanol. The solvent was removed under reduced pressure, and ethyl acetate was added to the resulting residue The mixture was washed with a 1N sodium hydroxide aqueous solution three times dried The solvent was removed under reduced pressure the resulting residue was purified by column chromatography The column was eluted with chloroform, chloroform containing methanol
Source ID: ord-d1ab5fb142a845ea85d6339642921aa8PubChem References
These sources are listed in the compound's public database record.
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