Aluminium lithium hydride → HCID 59715930, compound

HRID 2223718Notes

Reaction equation

HRID 2223718 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]([C@@H:16]([NH:20][C:21]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=[C:26]([CH3:34])[CH:25]=2)=[O:22])[CH:17]([CH3:19])[CH3:18])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C@@H:16]([NH:20][C:21]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=[C:26]([CH3:34])[CH:25]=2)=[O:22])[CH:17]([CH3:19])[CH3:18])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59715911HCID 59715911, compound

Product 1

HCID 59715930HCID 59715930, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[(S)-1-(4-benzyl-piperidine-1-carbonyl)-2-methyl-propyl]-3-(2-methyl-quinolin-4-yl)-urea in THF (10 mL) is added at 0° C. LiAlH4 (40 mg, 1 mmol). The reaction mixture is stirred at room temperature for 15 h and then quenched with EtOAc (1 mL) and sat. NaHCO3 (0.2 mL). The resulting precipitate is removed by filtration and the filtercake washed with MeOH (2×5 mL). The mixture is evaporated and the residue purified by TLC (SiO2, CH2Cl2/MeOH, 5/1) to provide the title compound.

Workup

  1. customquenched with EtOAc (1 mL) and sat. NaHCO3 (0.2 mL)
  2. customThe resulting precipitate is removed by filtration
  3. washthe filtercake washed with MeOH (2×5 mL)
  4. customThe mixture is evaporated
  5. customthe residue purified by TLC (SiO2, CH2Cl2/MeOH, 5/1)

Sources & evidence

ORD record
ord-e24b343c8a524ec8a1f2bf224630d05d
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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