HCID 2775915, compound → HCID 53215517, compound

HRID 889037Notes

Reaction equation

HRID 889037 reaction equation
O=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:5][CH:4]([C:17](O)=[O:18])[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C.C1COCC1>[F:15][C:13]([F:14])([F:16])[C:9]1[CH:8]=[C:7]([N:6]2[CH2:2][CH2:3][CH:4]([CH2:17][OH:18])[CH2:5]2)[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 2775915HCID 2775915, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 53215517HCID 53215517, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

5-Oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidine-3-carboxylic acid (0.35 g, 1.28 mmol) in diethyl ether (5 ml) was added to a solution of lithium aluminium hydride (0.097 g, 2.56 mmol) in THF (5 ml) at temperature 0° C. over a period of 10 min. The mixture was refluxed for 2 hours and then stirred at room temperature for 20 hours. The reaction mixture was diluted with diethyl ether (15 ml) and quenched with water (10 ml). The organic layer was separated and aqueous layer was extracted with diethyl ether. The combined organic layer was washed with saturated brine solution, dried over Na2SO4 and evaporated to obtain a residue which was purified by preparative TLC to afford [1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-yl]-methanol as a colorless mass (0.2 g, 64%).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customquenched with water (10 ml)
  3. customThe organic layer was separated
  4. extractionaqueous layer was extracted with diethyl ether
  5. washThe combined organic layer was washed with saturated brine solution
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customto obtain a residue which
  9. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-8a9de5f121b94039bcf782dc96bbb67a
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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