Sodium hydride → HCID 90051728, compound

HRID 2284661Notes

Reaction equation

HRID 2284661 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].[N+:14]([C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19]Br)([O-:16])=[O:15].C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[N+:14]([C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][O:11][CH2:10][CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 77569alpha-Bromo-2-nitrotolueneHCID 516892Sodium BicarbonateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 90051728HCID 90051728, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-Boc-ethanolamine (477 mg) in tetrahydrofuran (10 mL), sodium hydride (118 mg, 60 wt %) was added under ice cooling, and the mixture was stirred at the same temperature for 1 hour under a nitrogen atmosphere. To the reaction mixture, 2-nitrobenzyl bromide (500 mg) was added under ice cooling, and the mixture was stirred at the same temperature for 1 hour, and then further stirred at room temperature for 4 hours. To the reaction mixture, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 80 to 70% hexane in ethyl acetate) to obtain oily tert-butyl (2-((2-nitrobenzyl)oxy)ethyl)carbamate (C11, 154 mg).

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. stirringfurther stirred at room temperature for 4 hours
  3. customThe organic layer was separated
  4. washwashed successively with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (eluent, 80 to 70% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-d93f47c373df48388d3d757f80db4f66
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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