Aluminium lithium hydride → (2'-Fluoro-5'-(methyloxy)-2-(1-piperidinylmethyl)-1,1'-biphenyl-4-yl)methanol

HRID 1662462Notes

Reaction equation

HRID 1662462 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22](OC)=[O:23])=[CH:18][C:17]=1[CH2:26][N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C1COCC1.CCOC(C)=O>[F:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][OH:23])=[CH:18][C:17]=1[CH2:26][N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57705872Methyl 2'-fluoro-5'-(methyloxy)-2-(1-piperidinylmethyl)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57706303(2'-Fluoro-5'-(methyloxy)-2-(1-piperidinylmethyl)-1,1'-biphenyl-4-yl)methanolYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

LAH (1.0 M solution in THF) (0.55 mL, 0.55 mmol) was added to a solution of 66.64A (0.098 g, 0.27 mmol) in THF (5 mL). The resulting mixture was stirred at room temperature for 1 hour and then it was diluted with EtOAc, washed with water and brine, and dried over anhydrous Na2SO4. After removing solvent, 66.64B was obtained as a colorless oil in 100% yield.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. customAfter removing solvent

Sources & evidence

ORD record
ord-605500b00eb84cf8b32467eb91103d29
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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