N-Hydroxyphthalimide → 2-(cyclopropylmethoxy)-1H-isoindole-1,3(2H)-dione

To a suspension of cyclopropyl methanol (562 μl, 6.93 mmol), triphenylphosphine (2.02 g, 7.63 mmol) and N-hydroxyphthalimide (1.28 g, 7.63 mmol) in THF (10 mL) at 0° C. was added dropwise diethylazodicarboxylate (1.20 mL, 7.63 mmol) in THF (10 mL). The reaction mixture was allowed to stir for 15 h after which the solvent was removed under vacuum to dryness. Et2O (15 mL) was added to triturate the triphenylphosphine oxide and diethylhydrazinedicarboxylate, which was filtered off and washed with a little Et2O. The ethereal solution was concentrated under vacuum to give a residue which was filtered through a pad of silica (eluting with EtOAc/PE, 3:7). Removal of the solvent under reduced pressure afforded a pale yellow solid which was recrystallized from CH2Cl2/PE to give N-(cyclopropylmethoxy)phthalimide (1.30 g, 86%), as a white solid.

1. customwas removed under vacuum to dryness
2. additionEt2O (15 mL) was added
3. customto triturate the triphenylphosphine oxide and diethylhydrazinedicarboxylate, which
4. filtrationwas filtered off
5. washwashed with a little Et2O
6. concentrationThe ethereal solution was concentrated under vacuum
7. customto give a residue which
8. filtrationwas filtered through a pad of silica (eluting with EtOAc/PE, 3:7)
9. customRemoval of the solvent under reduced pressure
10. customafforded a pale yellow solid which
11. customwas recrystallized from CH2Cl2/PE

ORD record

ord-004be3464e64472eb4a5d7833a80fdba

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07906538B2