HCID 18512252, compound → HCID 18511948, compound

HRID 1370801Notes

Reaction equation

HRID 1370801 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](OC)=[O:27])=[CH:22][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 18512252HCID 18512252, compoundHCID 21225700Diisobutylaluminumhydride2×

Product 1

HCID 18511948HCID 18511948, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 6B (0.55 g, 1.4 mmoles) in THF (3.5 mL) was treated with diisobutylaluminum hydride (DIBAL) (2.94 mL, 2.94 mmoles, 1.0M in hexanes) dropwise at −78° C. After 30 minutes, an additional portion of DIBAL (1.5 mL) was added dropwise. After an additional 30 minutes, the acetone/dry ice bath was removed and the reaction mixture was carefully quenched with saturated NH4Cl. The mixture was diluted with diethyl ether (200 mL) and saturated sodium potassium tartrate (250 mL) and stirred vigorously for 2.5 hours. The two phases were separated and the organic phase was washed with brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 4:1→1:1 hexanes:ethyl acetate) to provide the title compound as a yellow oil (0.46 g, 91%).

Workup

  1. waitAfter an additional 30 minutes
  2. customthe acetone/dry ice bath was removed
  3. customthe reaction mixture was carefully quenched with saturated NH4Cl
  4. additionThe mixture was diluted with diethyl ether (200 mL) and saturated sodium potassium tartrate (250 mL)
  5. customThe two phases were separated
  6. washthe organic phase was washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated under reduced pressure
  10. customThe residue was purified by flash chromatography (silica gel, 4:1→1:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-8e93ca35a6774ee496856de9935dcc0d
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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