Diisobutylaluminum hydride → HCID 46240282, compound

HRID 471365Notes

Reaction equation

HRID 471365 reaction equation
[CH3:1][N:2]1[C:7](=O)[C:6]2=[C:9]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:15][CH:14]=3)[N:11]=[C:5]2[N:4]2[C@H:32]3[CH2:37][CH2:36][CH2:35][C@H:33]3[N:34]=[C:3]12.CC(C[AlH]CC(C)C)C>C1COCC1.C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH2:7][C:6]2=[C:9]([NH:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:10]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:17][CH:18]=3)[N:11]=[C:5]2[N:4]2[C@H:32]3[CH2:37][CH2:36][CH2:35][C@H:33]3[N:34]=[C:3]12

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydride2×HCID 11988837HCID 11988837, compound

Product 1

HCID 46240282HCID 46240282, compoundYield 11.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

(6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-Pyridin-2-yl)-benzyl)-cyclopent[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one (26.9 mg, 0.055 mmol) is dissolved in 1 mL of anhydrous THF, and then 400 uL of 1.5 M DIBAL-H in toluene is added dropwise. After the reaction mixture is stirred at room temperature overnight, additional 800 uL of 1.5 M DIBAL-His added to the solution. The reaction mixture is stirred at room temperature for 24 hours, and then quenched with NH4Cl aqueous solution. After routine workup, the mixture is purified by a semi-preparative HPLC to give 3.0 mg of pure product as while solids. MS (ESI) m/z 476.3 [M+H]+.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 24 hours
  2. customquenched with NH4Cl aqueous solution
  3. customAfter routine workup, the mixture is purified by a semi-preparative HPLC

Sources & evidence

ORD record
ord-55f1ca06fb774a408d166a0b98eec450
Source dataset
uspto-grants-2014_01
Patent number
US08633180B2

Reaction notes

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