Diisobutylaluminumhydride → HCID 21471554, compound

HRID 2294932Notes

Reaction equation

HRID 2294932 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH:13]3[CH2:18][CH2:17][CH:16]([C:19](OCC)=[O:20])[CH2:15][CH2:14]3)[CH2:9][CH2:8]2)[C:5]2[CH:24]=[CH:25][CH:26]=[CH:27][C:4]=2[NH:3]1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[O:1]=[C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][N:10]([CH:13]3[CH2:14][CH2:15][CH:16]([CH:19]=[O:20])[CH2:17][CH2:18]3)[CH2:11][CH2:12]2)[C:5]2[CH:24]=[CH:25][CH:26]=[CH:27][C:4]=2[NH:3]1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 21471545HCID 21471545, compound

Product 1

HCID 21471554HCID 21471554, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-90 °C

Procedure

To a stirred solution of the cis and trans isomers of ethyl 1-[4-(2-keto-1-benzimidazolinyl)piperidin-1-yl]cyclohexane-4-carboxylate (2.16 g) in dry toluene (150 mL) at -90° C. under argon, was added diisobutylaluminum hydride (11.6 mL of a 1.5M solution in toluene). The reaction mixture was stirred at -90° C. for 1 h, then quenched with methanol (1 mL) followed by saturated sodium potassium tartrate (50 mL). The layers were separated, the aqueous layer was extracted with 2×100 mL of ethyl acetate, and the combined organic layers were dried over MgSO4 and concentrated to dryness under reduced pressure to give the cis and trans isomers of 1-[4-(2-keto-1-benzimidazolinyl)piperidin-1-yl]cyclohexane-4-carboxaldehyde as a colorless foam (1.82 g).

Workup

  1. customquenched with methanol (1 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with 2×100 mL of ethyl acetate
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-84b9d6324c7b4f47aaa646991537ee39
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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