Diisobutylaluminum hydride → HCID 86602368, compound

HRID 1455842Notes

Reaction equation

HRID 1455842 reaction equation
C(NC(=O)C(N[C:13]([C:15]1[N:16]([CH3:44])[C:17]2[C:22]([C:23]=1[Cl:24])=[CH:21][C:20]([NH:25][C:26]([C:28]1[C:29]([C:34]3[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=3)=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:27])=[CH:19][CH:18]=2)=[O:14])C1C=CC=CC=1)C.CC(C[AlH]CC(C)C)C>C1COCC1.OS([O-])(=O)=O.[Na+].CCOC(C)=O>[Cl:24][C:23]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([NH:25][C:26]([C:28]3[C:29]([C:34]4[CH:39]=[CH:38][C:37]([C:40]([F:41])([F:43])[F:42])=[CH:36][CH:35]=4)=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:27])[CH:21]=2)[N:16]([CH3:44])[C:15]=1[CH:13]=[O:14]

Participants

6

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 22262741HCID 22262741, compound

Product 1

HCID 86602368HCID 86602368, compoundYield 51.2%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 516919Sodium BisulfateSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of the product from step (a) (1.56 g, 3.02 mmol) in THF (25 ml) at −78° C. was added DIBAL in THF (1.0 M, 12 ml), and the reaction mixture was stirred at −78° C. for 6 h. The reaction mixture was diluted with NaHSO4 (0.25 M, 86 ml) and EtOAc (115 ml), and the aqueous layer was extracted with EtOAc (2×100 ml). The combined organic layers were dried (MgSO4) and concentrated in vacuo to about 30 ml in volume. The product was purified by flash chromatography using 1:1 EtOAc/hexane to afford 0.706 g of the title compound.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc (2×100 ml)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo to about 30 ml in volume
  4. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-6f03be04996f481f9c7aeea0412cc58e
Source dataset
uspto-grants-2009_01
Patent number
US07482368B2

Reaction notes

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