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

Reaction equation

[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

Participants

Conditions

Temperature: 130 °C

Procedure

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.

Workup

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)

Sources & evidence

ORD record: ord-9a469fa7f5324139bbfd8a68ecc1fe1c
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530475B2

Linked notes

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