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

反応式

[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

参加物

反応条件

温度: 130 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード: ord-9a469fa7f5324139bbfd8a68ecc1fe1c
出典データセット: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08530475B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

関連ノート