N-Hydroxyphthalimide → 2-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propoxy]isoindole-1,3-dione

HRID 78997노트

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HRID 78997 반응식
[C:1]([Si:5]([CH3:12])([CH3:11])[O:6][C@@H:7]([CH3:10])[CH2:8][OH:9])([CH3:4])([CH3:3])[CH3:2].O[N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:1]([Si:5]([CH3:12])([CH3:11])[O:6][C@@H:7]([CH3:10])[CH2:8][O:9][N:14]1[C:18](=[O:19])[C:17]2[C:16](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]1=[O:24])([CH3:3])([CH3:4])[CH3:2]

참가 물질

6

반응물 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 15688069(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propan-1-ol

생성물 1

HCID 583743222-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propoxy]isoindole-1,3-dione

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of (S)-2-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol (53.0 g, 0.28 mol), N-hydroxyphthalimide (47.0 g, 0.29 mol) and triphenylphosphine (77.9 g, 0.30 mol) in THF (200 ml) at 0° C. was added dropwise DIAD (56.8 ml, 0.29 mol). During the addition the reagents dissolved and the solution turned a dark red colour before fading to pale yellow colour on completion of the addition. The reaction mixture was stirred and allowed to warm to room temperature overnight. The reaction mixture was concentrated in vacuo and the resultant residue re-dissolved in diethyl ether. The suspension was filtered and the filtrate was concentrated in vacuo to yield the crude title compound as a pale yellow oil. The material was used without further purification in the subsequent step.

후처리

  1. additionDuring the addition the reagents
  2. dissolutiondissolved
  3. additionbefore fading to pale yellow colour on completion of the addition
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. dissolutionthe resultant residue re-dissolved in diethyl ether
  6. filtrationThe suspension was filtered
  7. concentrationthe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-b60a2cb54444419c912959b2aecaceca
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841462B2

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