Diisobutylaluminumhydride → HCID 69922788, compound

HRID 2416546Notes

Reaction equation

HRID 2416546 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14](=O)/[CH:15]=[C:16](/[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:20][CH:19]=1)\[CH3:17])C>C(Cl)Cl>[N:25]1[CH:26]=[CH:27][CH:28]=[N:29][C:24]=1[C:21]1[CH:22]=[CH:23][C:18](/[C:16](/[CH3:17])=[CH:15]/[CH2:14][OH:13])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 69922546HCID 69922546, compound

Product 1

HCID 69922788HCID 69922788, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Diisobutylaluminum hydride (1.0 M solution in THF, 3.4 mL, 3.40 mmol) was added dropwise to a 0° C. solution of the product from step A (300 mg, 1.12 mmol) in methylene chloride (10 mL). The resulting solution was stirred for 20 min at 0° C., quenched with methanol (0.2 mL) followed by 15% aq. Rochelle salt (20 mL) and dichloromethane (10 mL), and allowed to stir at room temperature for 18 h. The layers were separated and the aqueous layer was extracted with methylene chloride (10 mL). The combined organic layers were washed with brine (20 mL), dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 3:2 hexane/ethyl acetate) provided 221 mg (87%) of the title compound as an off-white solid. MS 227 (M+H)+.

Workup

  1. customquenched with methanol (0.2 mL)
  2. stirringto stir at room temperature for 18 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with methylene chloride (10 mL)
  5. washThe combined organic layers were washed with brine (20 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customPurification by chromatography (SiO2, 3:2 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-37d5e432d36343e3b9356be4c16df16c
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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