Benzyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate → Benzyl (2-(aminooxy)ethyl)carbamate

HRID 710952Notes

Reaction equation

HRID 710952 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[NH:10][CH2:11][CH2:12][O:13][N:14]1C(=O)C2C(=CC=CC=2)C1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl>[NH2:14][O:13][CH2:12][CH2:11][NH:10][C:9](=[O:25])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 13983475Benzyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate

Product 1

HCID 13983481Benzyl (2-(aminooxy)ethyl)carbamateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl(2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate (9.36 g, 27.50 mmol) described in Reference Example 10 in methylene chloride (51 mL) was gradually added 9.8M methylamine methanol solution (8.50 mL), followed by stirring for 2 hours. The reaction solution was distilled off under reduced pressure, and methylene chloride (50 mL) and water (80 mL) were added, followed by adjusting to pH 1 with 5M hydrochloric acid, aqueous layer separation, and further washing with methylene chloride (50 mL). To the resulting aqueous layer was added methylene chloride (50 mL), followed by adjusting to pH11 with 5M sodium hydroxide, organic layer separation, and further extracting the aqueous layer with methylene chloride (50 mL) twice. The combined organic layers were washed with 50% potassium carbonate aqueous solution, followed by drying over anhydrous potassium carbonate, and distilling off the solvent under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate) to afford 5.61 g of the title compound (yield 97%).

Workup

  1. distillationThe reaction solution was distilled off under reduced pressure, and methylene chloride (50 mL) and water (80 mL)
  2. additionwere added
  3. customby adjusting to pH 1 with 5M hydrochloric acid, aqueous layer separation
  4. washfurther washing with methylene chloride (50 mL)
  5. additionTo the resulting aqueous layer was added methylene chloride (50 mL)
  6. customby adjusting to pH11 with 5M sodium hydroxide, organic layer separation
  7. extractionfurther extracting the aqueous layer with methylene chloride (50 mL) twice
  8. washThe combined organic layers were washed with 50% potassium carbonate aqueous solution
  9. dry with materialby drying over anhydrous potassium carbonate
  10. distillationdistilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-63df660da8124fc09124882a4f284eea
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

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