Aluminium lithium hydride → HCID 68511631, compound

HRID 1716597Notes

Reaction equation

HRID 1716597 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([C:11]([N:13]1[CH2:18][CH2:17][CH:16]([N:19]3[C:23]4[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:22]=4[N:21]=[C:20]3[C:29]([OH:32])([CH3:31])[CH3:30])[CH2:15][CH2:14]1)=O)[CH2:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([CH2:11][N:13]1[CH2:14][CH2:15][CH:16]([N:19]3[C:23]4[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:22]=4[N:21]=[C:20]3[C:29]([OH:32])([CH3:30])[CH3:31])[CH2:17][CH2:18]1)[CH2:5]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68513196HCID 68513196, compound

Product 1

HCID 68511631HCID 68511631, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of (5-amino-indan-2-yl)-{4-[2-(1-hydroxy-1-methyl-ethyl)-5-methyl-benzoimidazol-1-yl]-piperidin-1-yl}-methanone (150 mg, 0.35 mmol) in THF (10 mL) was added dropwise of 1 M lithium aluminum hydride (0.76 ml, 0.76 mmol) in THF. After stirring for 30 minutes, the reaction mixture was heated up to 80° C. and stirred for 20 minutes. The reaction mixture was quenched with water (0.3 ml) and 4 M NaOH solution (0.1 ml) at 0° C. The mixture was warmed up to rt and stirred for 45 minutes. The suspension was filtered over a Celite® pad, washed with ethyl acetate, and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography to afford 2-{1-[1-(5-amino-indan-2-ylmethyl)-piperidin-4-yl]-5-methyl-1H-benzoimidazol-2-yl}-propan-2-ol (87 mg, 60%) as a white solid.

Workup

  1. stirringstirred for 20 minutes
  2. customThe reaction mixture was quenched with water (0.3 ml) and 4 M NaOH solution (0.1 ml) at 0° C
  3. temperatureThe mixture was warmed up to rt
  4. stirringstirred for 45 minutes
  5. filtrationThe suspension was filtered over a Celite® pad
  6. washwashed with ethyl acetate
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-07bed6ea5e2a45cfb2b4aabe0bd315bc
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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