Diisobutylaluminumhydride → HCID 21841980, compound

HRID 1737213Notes

Reaction equation

HRID 1737213 reaction equation
[Cl:1][C:2]1[N:6]([C:7]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:8]=2[C:9](OC)=[O:10])[C:5](=[O:18])[N:4]([CH3:19])[N:3]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[Cl:1][C:2]1[N:6]([C:7]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:8]=2[CH2:9][OH:10])[C:5](=[O:18])[N:4]([CH3:19])[N:3]=1

Participants

4

Reactant 2

HCID 21225700Diisobutylaluminumhydride2×HCID 21841987HCID 21841987, compound

Product 1

HCID 21841980HCID 21841980, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of the title compound of Step C (7.0 g, 24.8 mmol) in dichloromethane (60 mL) cooled to -78° C. under a nitrogen atmosphere was added a 1 Molar solution of DIBAL (diisobutylaluminum hydride) in dichloromethane (62 mL, 62 mmol). After the addition was complete, the reaction mixture was allowed to warm to room temperature for 1 h. An additional portion of 1 Molar solution of DIBAL in dichloromethane (31 mL) was added at -78° C. and the mixture warmed to room temperature for 1 h. The reaction was quenched with 1 N HCl and extracted three times with dichloromethane. The combined organic phases were washed with saturated ammonium chloride solution, dried (MgSO4) and concentrated under reduced pressure. The residue was triturated to afford 4.4 g of the title compound of Step D as a solid. 1H NMR (CDCl3): δ 7.44 (apparent d,2H), 7.33 (t,1H), 4.46 (m,2H), 3.57 (s,3H), 2.66 m,1H), 2.18 (s,3H).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture warmed to room temperature for 1 h
  3. customThe reaction was quenched with 1 N HCl
  4. extractionextracted three times with dichloromethane
  5. washThe combined organic phases were washed with saturated ammonium chloride solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated

Sources & evidence

ORD record
ord-b333f2a3a33c436cbdfa2b191b51e6a2
Source dataset
uspto-grants-1999_10
Patent number
US05962436

Reaction notes

Loading…