Diisobutylaluminum hydride → Z-(1S,6S)-7-(2,4-Dimethoxy-benzyl)-9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene

HRID 40641

반응식

HRID 40641 반응식
[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][N:6]1[C:13](=O)[C@H:12]2[N:15]([C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=3)[C:16](=O)[C@@H:7]1[CH2:8][CH:9]=[CH:10][CH2:11]2.CC(C[AlH]CC(C)C)C>C1COCC1>[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][N:6]1[CH2:13][C@H:12]2[N:15]([C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=3)[CH2:16][C@@H:7]1[CH2:8][CH:9]=[CH:10][CH2:11]2

참가 물질

4

반응물 2

HCID 14487Diisobutylaluminum hydrideHCID 69230528Z-(1S,6S)-7-(2,4-Dimethoxy-benzyl)-9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene-8,10-dione

생성물 1

HCID 59686812Z-(1S,6S)-7-(2,4-Dimethoxy-benzyl)-9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
130 °C

실험 절차

Z-(1S,6S)-7-(2,4-Dimethoxy-benzyl)-9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene-8,10-dione (102 mg, 0.023 mmol), THF (1 mL) and DiBAl-H (6 mL, 6 mmol, [1M]) were placed in a μW tube under argon vent then heated to 130° C. for 900 sec. The reaction was quenched with Rochelle's solution and diethyl ether and the resulting mixture stirred overnight. The organic layer was separated and dried with magnesium sulfate, filtered and the solvent evaporated under reduced pressure to yield a crude oil, which was purified via reverse chromatography (20% CH3CN/water to 100% water) to yield the title compound as a residue.

후처리

  1. customThe reaction was quenched with Rochelle's solution and diethyl ether
  2. customThe organic layer was separated
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customto yield a crude oil, which
  7. customwas purified via reverse chromatography (20% CH3CN/water to 100% water)

출처 및 근거

ORD 기록
ord-9a469fa7f5324139bbfd8a68ecc1fe1c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530475B2

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