Sodium Hydroxide → {1-[2,4-Bis(trifluoromethyl)benzyl]azetidin-3-yl}methanol

HRID 1620483Notes

Reaction equation

HRID 1620483 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:9][CH:8]([C:10](OC)=[O:11])[CH2:7]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:7][CH:8]([CH2:10][OH:11])[CH2:9]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86678674Methyl 1-[2,4-bis(trifluoromethyl)benzyl]azetidine-3-carboxylate

Product 1

HCID 86678675{1-[2,4-Bis(trifluoromethyl)benzyl]azetidin-3-yl}methanolYield 57.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 1-[2,4-bis(trifluoromethyl)benzyl]azetidine-3-carboxylate (341 mg) in THF (5 mL) was added a suspension of lithium aluminum hydride (38 mg) in THF (5 mL) under ice-cooling. The reaction mixture was stirred at room temperature overnight. To the reaction mixture was added 1N aqueous sodium hydroxide solution under ice-cooling. The precipitate was removed by filtration, the filtrate was concentrated, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (180 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customThe precipitate was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-45e20b7672d94fbe8e0a92bc877e7fab
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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