Ethyl Acetate → HCID 90051729, compound

HRID 2284662Notes

Reaction equation

HRID 2284662 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[CH2:6][O:7][CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])([O-])=O.[Cl-].[NH4+].C(OCC)(=O)C>C(O)C.O.[Fe]>[NH2:1][C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[CH2:6][O:7][CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 90051728HCID 90051728, compound

Product 1

HCID 90051729HCID 90051729, compoundYield 43.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl (2-((2-nitrobenzyl)oxy)ethyl)carbamate (C11, 154 mg) in ethanol (5 mL) and water (1 mL), iron powder (174 mg) and ammonium chloride (167 mg) were added at room temperature, and the mixture was stirred at 80° C. for 2 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate was added to the reaction mixture. The insoluble matter was removed by filtration through Cerite, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (eluent, 75% hexane/25% ethyl acetate) to obtain oily tert-butyl (2-((2-aminobenzyl)oxy)ethyl)carbamate (C12, 60 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe insoluble matter was removed by filtration through Cerite
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by basic silica gel column chromatography (eluent, 75% hexane/25% ethyl acetate)

Sources & evidence

ORD record
ord-95c86f7a3e7245a3a289d6ee52c307a3
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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