Diisobutylaluminumhydride → HCID 22630973, compound

HRID 2416548Notes

Reaction equation

HRID 2416548 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13](=O)/[CH:14]=[CH:15]/[C:16]1[CH:17]=[N:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:20][CH:21]=1>C(Cl)Cl>[C:22]1([C:19]2[N:20]=[CH:21][C:16](/[CH:15]=[CH:14]/[CH2:13][OH:12])=[CH:17][N:18]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 69916936HCID 69916936, compound

Product 1

HCID 22630973HCID 22630973, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Diisobutylaluminum hydride (1.0 M solution in THF, 2.1 mL, 2.10 mmol) was added dropwise to a 0° C. solution of the product from step A (165 mg, 0.69 mmol) in methylene chloride (5 mL). The resulting solution was stirred for 15 min at 0° C., quenched with methanol (0.5 mL) followed by 15% aq. Rochelle salt (15 mL) and dichloromethane (5 mL), and allowed to stir at room temperature for 18 h. The layers were separated and the aqueous layer was extracted with methylene chloride (5 mL). The combined organic layers were dried (MgSO4) and concentrated to provide 140 mg (96%) of the title compound as a colorless solid. MS 213 (M+H)+.

Workup

  1. customquenched with methanol (0.5 mL)
  2. stirringto stir at room temperature for 18 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with methylene chloride (5 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e479d2653f8a43678884658bbf18883b
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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