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

HRID 602599노트

반응식

HRID 602599 반응식
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:26]1[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:1]1([CH2:4][O:5][N:26]2[C:27](=[O:36])[C:28]3=[CH:35][CH:34]=[CH:33][CH:32]=[C:29]3[C:30]2=[O:31])[CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 75644CyclopropanemethanolHCID 5462977Diethyl azodicarboxylate

생성물 1

HCID 14843102-(cyclopropylmethoxy)-1H-isoindole-1,3(2H)-dione수율 86.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-004be3464e64472eb4a5d7833a80fdba
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906538B2

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