Aluminium lithium hydride → (2-((2,6-Dimethyl-1-piperidinyl)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanol

HRID 1662473Notes

Reaction equation

HRID 1662473 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH3:14])[N:9]1[CH2:15][C:16]1[CH:21]=[C:20]([C:22](OC)=[O:23])[CH:19]=[CH:18][C:17]=1[C:26]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=1[F:34]>C1COCC1.[Cl-].[Na+].O>[CH3:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH3:14])[N:9]1[CH2:15][C:16]1[CH:21]=[C:20]([CH2:22][OH:23])[CH:19]=[CH:18][C:17]=1[C:26]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=1[F:34]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57705951Methyl 2-((2,6-dimethyl-1-piperidinyl)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57705743(2-((2,6-Dimethyl-1-piperidinyl)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanolYield 69.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

LAH (1.0 M solution in THF) (0.088 mL, 0.088 mmol) was added slowly to a solution of 66.69B (0.034 g, 0.088 mmol) in THF (1 mL). The resulting mixture was stirred at room temperature for 25 minutes and then was poured into brine (2 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were dried over anhydrous sodium sulfate. After removing solvent, the residue was purified by flash chromatography (silica gel, 1:1 EtOAc/hexane) and gave 66.69C (22 mg) as a colorless oil.

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. customAfter removing solvent
  4. customthe residue was purified by flash chromatography (silica gel, 1:1 EtOAc/hexane)

Sources & evidence

ORD record
ord-77425a969c544e7fa0a457ecbadaba2d
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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