Diisobutylaluminumhydride → HCID 58123729, compound

HRID 1616670Notes

Reaction equation

HRID 1616670 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([N:18]1[C:25](=O)[CH2:24][CH:23]2[CH2:27][CH:19]1[CH2:20][CH2:21][CH:22]2[O:28]C(=O)C)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[CH2:11]([N:18]1[CH2:25][CH2:24][CH:23]2[CH2:27][CH:19]1[CH2:20][CH2:21][CH:22]2[OH:28])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 66942372HCID 66942372, compound

Product 1

HCID 58123729HCID 58123729, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-70 °C

Procedure

Diisobutylaluminum hydride (1.5 mol/L in toluene, 21 mL) is added to a solution of acetic acid 2-benzyl-3-oxo-2-aza-bicyclo[3.3.1]non-6-yl ester (1.50 g, for synthesis see J. Chem. Soc. Perkin Trans. 1 1999, 1157-1162) in toluene (30 mL) cooled to −70° C. The cooling bath is removed and the solution is stirred at ambient temperature overnight. Then, another portion of diisobutylaluminum hydride (1.5 mol/L in toluene, 20 mL) is added and the solution is stirred for additional 4 h at room temperature. Then, the solution is poured into ice-cold water and the resulting mixture is extracted with ethyl acetate. The aqueous phase is acidified using 4 M hydrochloric acid and extracted one more time with ethyl acetate. The combined organic extracts are dried (Na2SO4) and the solvent is removed. The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→2:1).

Workup

  1. customThe cooling bath is removed
  2. additionThen, another portion of diisobutylaluminum hydride (1.5 mol/L in toluene, 20 mL) is added
  3. stirringthe solution is stirred for additional 4 h at room temperature
  4. additionThen, the solution is poured into ice-cold water
  5. extractionthe resulting mixture is extracted with ethyl acetate
  6. extractionextracted one more time with ethyl acetate
  7. dry with materialThe combined organic extracts are dried (Na2SO4)
  8. customthe solvent is removed
  9. customThe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→2:1)

Sources & evidence

ORD record
ord-1d1645c3e55a4adc8aa275eca92bcd20
Source dataset
uspto-grants-2014_07
Patent number
US08765780B2

Reaction notes

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