Reaction #4168354
Related Literature (1)
openreactiondata ↗doi:10.1039/C8SC04228D
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-24c36fe476a344bcad2d9364a561f0e6No renderable structure data available
CC(C)C(CO)NC(=O)OCC1=CC=CC=C1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | benzyl N-(1-hydroxy-3-methylbutan-2-yl)carbamate |
|---|---|
| IUPAC Name | — |
| CAS Number | 1356582-71-2 |
| Database ID | 14036742 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
benzyl N-(1-hydroxy-3-methylbutan-2-yl)carbamate (CAS 1356582-71-2) 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 14036742
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
11 reactions · 11 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-24c36fe476a344bcad2d9364a561f0e6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-00edffd994924de19152d331f4e392d4Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-24c36fe476a344bcad2d9364a561f0e6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 11.0 g (0.0464 mole) of benzyl N-[1-(hydroxymethyl)-2-methyl-propyl]carbamate in dioxane (100 mL) cooled to 0° C. was added diphenylphosphoryl azide 10.99 mL (1.1 eq) followed by the addition of DBU 8.32 mL (1.2 eq). The contents were allowed to warm to room temperature and stirred for 16 hrs. After the addition of ethyl acetate (300 mL) and water (100 mL), the organic layer was separated and then washed with satd. NaHCO3 (100 mL). The organic layer was then dried (magnesium sulfate) and then concentrated under vacuum. To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g and the contents then heated to 90 degrees for 2 hrs. After addition of ethyl acetate and water the layers were separated. The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that was columned using hexane/ethyl acetate (0-70%) to afford benzyl N-[1-(azidomethyl)-2-methyl-propyl]carbamate 6.9 g as a colorless oil. the organic layer was separated washed with satd The organic layer was then dried (magnesium sulfate) concentrated under vacuum To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g the contents then heated to 90 degrees for 2 hrs After addition of ethyl acetate and water the layers were separated The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that
Source ID: ord-eabdf904f91b4a06b36fd709ac0f20deConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 11.0 g (0.0464 mole) of benzyl N-[1-(hydroxymethyl)-2-methyl-propyl]carbamate in dioxane (100 mL) cooled to 0° C. was added diphenylphosphoryl azide 10.99 mL (1.1 eq) followed by the addition of DBU 8.32 mL (1.2 eq). The contents were allowed to warm to room temperature and stirred for 16 hrs. After the addition of ethyl acetate (300 mL) and water (100 mL), the organic layer was separated and then washed with satd. NaHCO3 (100 mL). The organic layer was then dried (magnesium sulfate) and then concentrated under vacuum. To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g and the contents then heated to 90 degrees for 2 hrs. After addition of ethyl acetate and water the layers were separated. The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that was columned using hexane/ethyl acetate (0-70%) to afford benzyl N-[1-(azidomethyl)-2-methyl-propyl]carbamate 6.9 g as a colorless oil. the organic layer was separated washed with satd The organic layer was then dried (magnesium sulfate) concentrated under vacuum To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g the contents then heated to 90 degrees for 2 hrs After addition of ethyl acetate and water the layers were separated The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that
Source ID: ord-be427f50757a4a0eaa312ee0ab0070e2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 11.0 g (0.0464 mole) of benzyl N-[1-(hydroxymethyl)-2-methyl-propyl]carbamate in dioxane (100 mL) cooled to 0° C. was added diphenylphosphoryl azide 10.99 mL (1.1 eq) followed by the addition of DBU 8.32 mL (1.2 eq). The contents were allowed to warm to room temperature and stirred for 16 hrs. After the addition of ethyl acetate (300 mL) and water (100 mL), the organic layer was separated and then washed with satd. NaHCO3 (100 mL). The organic layer was then dried (magnesium sulfate) and then concentrated under vacuum. To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g and the contents then heated to 90 degrees for 2 hrs. After addition of ethyl acetate and water the layers were separated. The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that was columned using hexane/ethyl acetate (0-70%) to afford benzyl N-[1-(azidomethyl)-2-methyl-propyl]carbamate 6.9 g as a colorless oil. the organic layer was separated washed with satd The organic layer was then dried (magnesium sulfate) concentrated under vacuum To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g the contents then heated to 90 degrees for 2 hrs After addition of ethyl acetate and water the layers were separated The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that
Source ID: ord-be427f50757a4a0eaa312ee0ab0070e2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 11.0 g (0.0464 mole) of benzyl N-[1-(hydroxymethyl)-2-methyl-propyl]carbamate in dioxane (100 mL) cooled to 0° C. was added diphenylphosphoryl azide 10.99 mL (1.1 eq) followed by the addition of DBU 8.32 mL (1.2 eq). The contents were allowed to warm to room temperature and stirred for 16 hrs. After the addition of ethyl acetate (300 mL) and water (100 mL), the organic layer was separated and then washed with satd. NaHCO3 (100 mL). The organic layer was then dried (magnesium sulfate) and then concentrated under vacuum. To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g and the contents then heated to 90 degrees for 2 hrs. After addition of ethyl acetate and water the layers were separated. The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that was columned using hexane/ethyl acetate (0-70%) to afford benzyl N-[1-(azidomethyl)-2-methyl-propyl]carbamate 6.9 g as a colorless oil. the organic layer was separated washed with satd The organic layer was then dried (magnesium sulfate) concentrated under vacuum To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g the contents then heated to 90 degrees for 2 hrs After addition of ethyl acetate and water the layers were separated The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that
Source ID: ord-abca417b52c74be1812a89820e2da0b3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 11.0 g (0.0464 mole) of benzyl N-[1-(hydroxymethyl)-2-methyl-propyl]carbamate in dioxane (100 mL) cooled to 0° C. was added diphenylphosphoryl azide 10.99 mL (1.1 eq) followed by the addition of DBU 8.32 mL (1.2 eq). The contents were allowed to warm to room temperature and stirred for 16 hrs. After the addition of ethyl acetate (300 mL) and water (100 mL), the organic layer was separated and then washed with satd. NaHCO3 (100 mL). The organic layer was then dried (magnesium sulfate) and then concentrated under vacuum. To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g and the contents then heated to 90 degrees for 2 hrs. After addition of ethyl acetate and water the layers were separated. The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that was columned using hexane/ethyl acetate (0-70%) to afford benzyl N-[1-(azidomethyl)-2-methyl-propyl]carbamate 6.9 g as a colorless oil. the organic layer was separated washed with satd The organic layer was then dried (magnesium sulfate) concentrated under vacuum To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g the contents then heated to 90 degrees for 2 hrs After addition of ethyl acetate and water the layers were separated The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that
Source ID: ord-a806eec36bb84fa08a0e8ec389c60e89Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 11.0 g (0.0464 mole) of benzyl N-[1-(hydroxymethyl)-2-methyl-propyl]carbamate in dioxane (100 mL) cooled to 0° C. was added diphenylphosphoryl azide 10.99 mL (1.1 eq) followed by the addition of DBU 8.32 mL (1.2 eq). The contents were allowed to warm to room temperature and stirred for 16 hrs. After the addition of ethyl acetate (300 mL) and water (100 mL), the organic layer was separated and then washed with satd. NaHCO3 (100 mL). The organic layer was then dried (magnesium sulfate) and then concentrated under vacuum. To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g and the contents then heated to 90 degrees for 2 hrs. After addition of ethyl acetate and water the layers were separated. The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that was columned using hexane/ethyl acetate (0-70%) to afford benzyl N-[1-(azidomethyl)-2-methyl-propyl]carbamate 6.9 g as a colorless oil. the organic layer was separated washed with satd The organic layer was then dried (magnesium sulfate) concentrated under vacuum To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g the contents then heated to 90 degrees for 2 hrs After addition of ethyl acetate and water the layers were separated The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that
Source ID: ord-4604cb0e626742c0a03f156580b389d2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 11.0 g (0.0464 mole) of benzyl N-[1-(hydroxymethyl)-2-methyl-propyl]carbamate in dioxane (100 mL) cooled to 0° C. was added diphenylphosphoryl azide 10.99 mL (1.1 eq) followed by the addition of DBU 8.32 mL (1.2 eq). The contents were allowed to warm to room temperature and stirred for 16 hrs. After the addition of ethyl acetate (300 mL) and water (100 mL), the organic layer was separated and then washed with satd. NaHCO3 (100 mL). The organic layer was then dried (magnesium sulfate) and then concentrated under vacuum. To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g and the contents then heated to 90 degrees for 2 hrs. After addition of ethyl acetate and water the layers were separated. The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that was columned using hexane/ethyl acetate (0-70%) to afford benzyl N-[1-(azidomethyl)-2-methyl-propyl]carbamate 6.9 g as a colorless oil. the organic layer was separated washed with satd The organic layer was then dried (magnesium sulfate) concentrated under vacuum To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g the contents then heated to 90 degrees for 2 hrs After addition of ethyl acetate and water the layers were separated The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that
Source ID: ord-c0c64c56c88c49c8b0ff827b866ca7dbConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 11.0 g (0.0464 mole) of benzyl N-[1-(hydroxymethyl)-2-methyl-propyl]carbamate in dioxane (100 mL) cooled to 0° C. was added diphenylphosphoryl azide 10.99 mL (1.1 eq) followed by the addition of DBU 8.32 mL (1.2 eq). The contents were allowed to warm to room temperature and stirred for 16 hrs. After the addition of ethyl acetate (300 mL) and water (100 mL), the organic layer was separated and then washed with satd. NaHCO3 (100 mL). The organic layer was then dried (magnesium sulfate) and then concentrated under vacuum. To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g and the contents then heated to 90 degrees for 2 hrs. After addition of ethyl acetate and water the layers were separated. The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that was columned using hexane/ethyl acetate (0-70%) to afford benzyl N-[1-(azidomethyl)-2-methyl-propyl]carbamate 6.9 g as a colorless oil. the organic layer was separated washed with satd The organic layer was then dried (magnesium sulfate) concentrated under vacuum To this intermediate in DMSO (100 mL) was added sodium azide 7.54 g the contents then heated to 90 degrees for 2 hrs After addition of ethyl acetate and water the layers were separated The organic layer was dried with magnesium sulfate followed by concentration under vacuum to afford an oil that
Source ID: ord-eabdf904f91b4a06b36fd709ac0f20dePubChem References
These sources are listed in the compound's public database record.
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