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

HRID 1662456Notes

Reaction equation

HRID 1662456 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16](OC)=[O:17])=[CH:12][C:11]=1[CH:20]1[CH2:24][CH2:23][CH2:22][CH:21]1[CH3:25].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][C:11]=1[CH:20]1[CH2:24][CH2:23][CH2:22][CH:21]1[CH3:25]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57706176Methyl 2'-fluoro-2-(2-methylcyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57706147(2'-Fluoro-2-(2-methylcyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanolYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 200 mL round bottom flask was charged with 66.56G (0.31 g, 0.91 mmol) and THF (10 mL). To the solution was added LAH (1.0 M in THF) (0.91 mL, 0.91 mmol) dropwise at room temperature. The resulting solution was stirred for 15 minutes, quenched with saturated aqueous Rochelle salt, and extracted with ether. The combined organic layers were dried (MgSO4) and concentrated. The initial product was purified by silica gel flash chromatography (0-30% EtOAc/hexane) to afford 66.56H (mixture of diastereomers) (0.27 g, 95% yield) as a colorless oil.

Workup

  1. customquenched with saturated aqueous Rochelle salt
  2. extractionextracted with ether
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. customThe initial product was purified by silica gel flash chromatography (0-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-07e149b26d594e878df1c5bd5b440cdd
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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