Aluminium lithium hydride → HCID 178444680, compound

HRID 353124Notes

Reaction equation

HRID 353124 reaction equation
[CH2:1]([S:8][C:9]1[NH:10][CH:11]=[C:12]([C:14]2[CH:15]=[C:16]([C:20]3([CH3:34])[CH2:25][CH2:24][N:23]([C:26](=O)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:22][CH:21]3[CH3:33])[CH:17]=[CH:18][CH:19]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([S:8][C:9]1[NH:10][CH:11]=[C:12]([C:14]2[CH:15]=[C:16]([C:20]3([CH3:34])[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:22][CH:21]3[CH3:33])[CH:17]=[CH:18][CH:19]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178445104HCID 178445104, compound

Product 1

HCID 178444680HCID 178444680, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-(2-(benzylsulfanyl)-1H-imidazol-4-yl)phenyl)-1-hexanoyl-3,4-dimethylpiperidine (Preparation 41, 101 mg, 0.21 mmol) in tetrahydrofuran (2 mL) at 0° C. was added lithium aluminium hydride (1.0 M solution in tetrahydrofuran, 0.32 mL, 0.32 mmol) dropwise over a few minutes. The solution was stirred at room temperature under a nitrogen atmosphere for 1 h and then cooled back to 0° C. The reaction was cautiously quenched by the addition of 1 N sodium hydroxide (0.5 mL) and then ethyl acetate (10 mL) and solid sodium hydrogen-carbonate (excess) were added. The mixture was stirred vigorously for 30 minutes and then filtered through Celite®, washing with ethyl acetate. The filtrate was concentrated in vacuo to give the title compound as a clear oil (98 mg, 100%).

Workup

  1. temperaturecooled back to 0° C
  2. customThe reaction was cautiously quenched by the addition of 1 N sodium hydroxide (0.5 mL)
  3. additionethyl acetate (10 mL) and solid sodium hydrogen-carbonate (excess) were added
  4. stirringThe mixture was stirred vigorously for 30 minutes
  5. filtrationfiltered through Celite®
  6. washwashing with ethyl acetate
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-57c4115cd7e4455f91bff6fa048e0e46
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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