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

HRID 1662475Notes

Reaction equation

HRID 1662475 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C@@H:8]1[CH2:12][CH2:11][C@@H:10]([CH3:13])[N:9]1[CH2:14][C:15]1[CH:20]=[C:19]([C:21](OC)=[O:22])[CH:18]=[CH:17][C:16]=1[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=1[F:33]>C1COCC1.[Cl-].[Na+].O>[CH3:7][C@@H:8]1[CH2:12][CH2:11][C@@H:10]([CH3:13])[N:9]1[CH2:14][C:15]1[CH:20]=[C:19]([CH2:21][OH:22])[CH:18]=[CH:17][C:16]=1[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=1[F:33]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57705891Methyl 2-(((2R,5R)-2,5-dimethyl-1-pyrrolidinyl)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57706802(2-(((2R,5R)-2,5-Dimethyl-1-pyrrolidinyl)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanolYield 98.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

LAH (1.0 M solution in THF) (0.086 mL, 0.086 mmol) was added slowly to a solution of 66.71A (0.032 g, 0.086 mmol) in THF (1.5 mL) and the mixture was stirred at room temperature for 33 minutes. The mixture was poured into brine (2 mL) and extracted with EtOAc (3×30 mL). The combined organic phase was dried over anhydrous sodium sulfate and filtered. After removing solvent, 66.71B (29 mg) was obtained.

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customAfter removing solvent

Sources & evidence

ORD record
ord-0a276d871eee40059ca6cccc1e2d7fd3
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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