Aluminium lithium hydride → HCID 178444684, compound

HRID 353121Notes

Reaction equation

HRID 353121 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[N:22]=[N:23][NH:24][C:25]=3[F:26])[CH:16]=2)([CH3:14])[CH:10]([CH3:27])[CH2:9]1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[F:26][C:25]1[NH:24][N:23]=[N:22][C:21]=1[C:17]1[CH:16]=[C:15]([C:11]2([CH3:14])[CH2:12][CH2:13][N:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:9][CH:10]2[CH3:27])[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178445105HCID 178445105, compound

Product 1

HCID 178444684HCID 178444684, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-hexanoyl-4-(3-(5-fluoro-1H-1,2,3-triazol-4-yl)phenyl)-3,4-dimethylpiperidine (Preparation 30, 20 mg, 0.054 mmol) in diethyl ether (0.8 mL) at 0° C. was added lithium aluminium hydride (1.0 M solution in tetrahydrofuran, 54 μL, 0.054 mmol) dropwise. The solution was then heated at reflux under a nitrogen atmosphere for 30 minutes before it was cooled back to 0° C. The reaction was cautiously quenched by the addition of 1 N sodium hydroxide (0.2 mL) and then ethyl acetate (3.0 mL) and solid sodium hydrogencarbonate were added. The mixture was stirred vigorously for 30 minutes and then filtered, washing with ethyl acetate. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with ethyl acetate:hexane (2:1). The title compound was isolated as clear oil (8.0 mg, 40%).

Workup

  1. temperatureThe solution was then heated
  2. temperatureat reflux under a nitrogen atmosphere for 30 minutes before it
  3. customThe reaction was cautiously quenched by the addition of 1 N sodium hydroxide (0.2 mL)
  4. additionethyl acetate (3.0 mL) and solid sodium hydrogencarbonate were added
  5. filtrationfiltered
  6. washwashing with ethyl acetate
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate:hexane (2:1)

Sources & evidence

ORD record
ord-c0a94c6dd4454928aa08229478cfd96b
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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