Phthalimide → 1H-Isoindole-1,3(2H)-dione, 4-amino-

A mixture of 4 g (21 mmol) of the preceeding diamine, 4.6 g (21 mmol) of di-tert-butyl dicarbonate, and 100 mL of dry CH2Cl2 was stirred for 12 hours at room temperature. Solvent and volatile by-products were removed by evaporation under reduced pressure, leaving 6 g (100% yield) of 6-(tert-butyloxycarbonylamino)-1-diethylamino-2-hydroxyhexane as an oil which was not further purified. It was dissolved in 100 mL of dry tetrahydrofuran (THF) along with 3.27 g (22 mmol) of phthalimide, 5.77 g (22 mmol) of triphenylphosphine, and 3.83 g (22 mmol) of diethyl azodicarboxylate (DEAD). The solution was stirred at room temperature for 12 hours at which point, to complete the reaction, an additional 1.64 g (11 mmol) of phthalimide and 1.92 g (11 mmol) of DEAD were added and stirring continued for 1 hour. Solvent was removed and the residual oil partitioned between ether and 1% hydrochloric acid. The aqueous phase was separated, made basic with NaOH solution, and extracted with ether. The ether extract was dried over anhydrous MgSO4, filtered and evaporated. A pale yellow oil resulted which was dried under high vacuum to afford 9.2 g of the protected amino-phthalimide as a pale yellow oil.

1. customthe reaction
2. stirringstirring
3. waitcontinued for 1 hour
4. customSolvent was removed
5. customthe residual oil partitioned between ether and 1% hydrochloric acid
6. customThe aqueous phase was separated
7. extractionextracted with ether
8. extractionThe ether extract
9. dry with materialwas dried over anhydrous MgSO4
10. filtrationfiltered
11. customevaporated
12. customA pale yellow oil resulted which
13. customwas dried under high vacuum

ORDレコード

ord-f63b7201ce9345c7aa3c2f8f2d0d0f9a

出典データセット

uspto-grants-1987_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04673763