N-Hydroxyphthalimide → 2-(tetrahydro-2H-pyran-4-yloxy)-1H-isoindole-1,3(2H)-dione

HRID 29162

반응식

HRID 29162 반응식
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:32]1[CH2:37][CH2:36][CH:35](O)[CH2:34][CH2:33]1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[O:32]1[CH2:37][CH2:36][CH:35]([O:1][N:2]2[C:3](=[O:12])[C:4]3[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:7])[CH2:34][CH2:33]1

참가 물질

6

반응물 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 97268Di-tert-butyl azodicarboxylate

생성물 1

HCID 229971882-(tetrahydro-2H-pyran-4-yloxy)-1H-isoindole-1,3(2H)-dione

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A light suspension containing N-hydroxylphthalimide (18.4 mmol, 3.0 g), triphenylphosphine (18.4 mmol, 4.82 g), tetrahydro-4H-pyran-4-ol (18.4 mmol, 1.75 mL) and anhydrous THF (50 mL), were transferred to a flask containing di-tert-butyl azodicarboxylate (20.2 mmol, 4.66 g) under nitrogen. Over 2 hours the reaction stirred at room temperature and changed from a dark orange to yellow in appearance. The solvent was removed under vacuum and replaced with trifluoroacetic acetic acid (10 mL). The reaction was stirred for 30 minutes and the TFA was removed under vacuum. The crude residue was then dissolved in ethyl acetate, washed with a saturated aqueous solution of sodium bicarbonate, 5% aqueous solution of potassium carbonate, brine and dried over magnesium sulfate. The solvent was removed under vacuum and the residual triphenylphosphine oxide was crystallized and filtered using hexanes and ether. The solvent was again removed and the crude solid was purified by silica gel chromatography (2:1 hexanes/ethyl acetate) and recrystallization using methylene chloride and hexanes providing 1.69 g (37%) of a white crystal. Rf=0.3 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.84-7.82 (2H,m), 7.75-7.73(2H,m), 4.46-4.40 (1H,m), 4.08-4.02 (2H,m), 3.50-3.44 (2H,m), 2.04-1.98 (2H,m), 1.92-1.84 (2H,m).

후처리

  1. customwere transferred to a flask
  2. customThe solvent was removed under vacuum
  3. stirringThe reaction was stirred for 30 minutes
  4. customthe TFA was removed under vacuum
  5. dissolutionThe crude residue was then dissolved in ethyl acetate
  6. washwashed with a saturated aqueous solution of sodium bicarbonate, 5% aqueous solution of potassium carbonate, brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed under vacuum
  9. customthe residual triphenylphosphine oxide was crystallized
  10. filtrationfiltered
  11. customThe solvent was again removed
  12. customthe crude solid was purified by silica gel chromatography (2:1 hexanes/ethyl acetate) and recrystallization

출처 및 근거

ORD 기록
ord-fce6c1405a3f40fe8d7a6b21743c7f28
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419967B2

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