Aluminium lithium hydride → HCID 21901922, compound

HRID 720058Notes

Reaction equation

HRID 720058 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:25]=[CH:24][C:6]([O:7][CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([CH:17]3[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]3)=O)[CH2:10]2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:26][C:2]([F:1])([F:27])[C:3]1[CH:25]=[CH:24][C:6]([O:7][CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH:17]3[CH2:18][CH2:19][CH:20]([OH:23])[CH2:21][CH2:22]3)[CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21901997HCID 21901997, compound

Product 1

HCID 21901922HCID 21901922, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-[3-(4-Trifluoromethyl-phenoxymethyl)-piperidine-1-carbonyl]-cyclohexanone (27 mg, 0.070 mmol) was dissolved in 1 mL of THF and excess lithium aluminum hydride (27 mg, ca. 10 equivalents) was added. The solution was heated to reflux for 5 minutes, cooled to 0° C., and quenched by dropwise addition of 0.5 mL 1M NaOH. Additional THF (10 mL) was added, and the suspension was stirred at room temperature for 30 minutes and then filtered though a plug of sodium sulfate. The solution thus obtained was concentrated in vacuo and the residue was purified by flash chromatography on silica gel using as eluent a gradient of ethyl acetate in hexane containing 1% ammonium hydroxide. 4-[3-(4-Trifluoromethyl-phenoxymethyl)-piperidin-1-ylmethyl]-cyclohexanol, 188, (16 mg, 61%) was obtained. Data for this compound: MS 372 (M++1).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 5 minutes
  3. customquenched by dropwise addition of 0.5 mL 1M NaOH
  4. additionAdditional THF (10 mL) was added
  5. filtrationfiltered though a plug of sodium sulfate
  6. customThe solution thus obtained
  7. concentrationwas concentrated in vacuo
  8. customthe residue was purified by flash chromatography on silica gel using as eluent a gradient of ethyl acetate in hexane containing 1% ammonium hydroxide

Sources & evidence

ORD record
ord-4e5424ce3d804f5e82b15764d4aa83ab
Source dataset
uspto-grants-2006_11
Patent number
US07132551B2

Reaction notes

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