Diisobutylaluminumhydride → HCID 19008896, compound

HRID 1742413Notes

Reaction equation

HRID 1742413 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH2:22][CH2:23][CH2:24][CH3:25])[N:9]([CH:12]2[C:20]3[C:15](=[CH:16][C:17]([Br:21])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[C:10]=1[Cl:11])=O)C.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[Br:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[CH:12]([N:9]1[C:10]([Cl:11])=[C:6]([CH2:4][OH:3])[N:7]=[C:8]1[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:13][CH2:14]2

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 54352161HCID 54352161, compound

Product 1

HCID 19008896HCID 19008896, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(5-bromo-indan-1-yl)-2-butyl-5-chloro-1H-imidazole-4-carboxylic acid ethyl ester (486 mg, 1.13 mmol)in CH2Cl2 (5.0 mL) at 0° C. was added diisobutylaluminum hydride (Dibal-H) (1M solution in CH2Cl2, 5.0 mL). The reaction mixture was allowed to warm to room temperature and was stirred for 0.75 hour, carefully quenched with saturated aqueous NH4Cl (1 mL) and diluted with CH2Cl2 (100 mL). The organic solution was separated and washed with saturated aqueous NaHCO3 (2×10 mL), saturated aqueous NaCl (2×10 mL), dried (MgSO4) and concentrated in vacuo. The crude residue was chromatographed on SiO2 -gel using 100% EtOAC to give 400 mg of a colorless oil. 1H NMR (250 MHz, d6 -DMSO): d 7.55 (s, 1 H), 7.36 (d, 1 H), 6.83 (d, 1 H), 5.95 (t, 1 H), 4.85 (bs, 1 H), 4.18 (s, 2 H), 3.05 (m, 2 H), 2.70 (m, 3 H), 2.26 (m, 1 H), 1.64 (m, 2 H), 1.30 (m, 2 H), 0.90 (m, 3 H).

Workup

  1. customcarefully quenched with saturated aqueous NH4Cl (1 mL)
  2. additiondiluted with CH2Cl2 (100 mL)
  3. customThe organic solution was separated
  4. washwashed with saturated aqueous NaHCO3 (2×10 mL), saturated aqueous NaCl (2×10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was chromatographed on SiO2

Sources & evidence

ORD record
ord-ecdff55fc6e848eaa0911a2976d4866e
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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