Diisobutylaluminum hydride → HCID 86602368, compound

HRID 490007Notes

Reaction equation

HRID 490007 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

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 co 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-77ff074f8d1d49e6bd4757898fe42f14
Source dataset
uspto-grants-2005_12
Patent number
US06979692B2

Reaction notes

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