tert-Butyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate → tert-butyl N-(2-(aminooxy)ethyl)carbamate

To a solution of tert-butyl(2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate (1.83 g, 6.00 mmol) described in Reference Example 7 in methylene chloride (11 mL) was gradually added 9.8M methylamine methanol solution (1.83 mL), followed by stirring for 2 hours. The reaction solution was filtered and the filtrate was distilled off under reduced pressure, followed by extracting with 0.5M hydrochloric acid (24 mL). To the resulting aqueous layer were added methylene chloride and 1M sodium hydroxide (18 mL), thereby the target was extracted with ethylene chloride. The resulting organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. 1.038 g of the title compound was afforded as the crude product (yield 98%).

1. filtrationThe reaction solution was filtered
2. distillationthe filtrate was distilled off under reduced pressure
3. extractionby extracting with 0.5M hydrochloric acid (24 mL)
4. additionTo the resulting aqueous layer were added methylene chloride and 1M sodium hydroxide (18 mL)
5. extractionthe target was extracted with ethylene chloride
6. dry with materialThe resulting organic layer was dried over magnesium sulfate
7. distillationthe solvent was distilled off under reduced pressure

ORD record

ord-7897e383c4f843128b57f59ff7fd09ed

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181250B2