Sodium hydride → (S)-2-((1-methylpyrrolidin-2-yl)methoxy)-5-(trifluoromethyl)benzonitrile

HRID 1931083Notes

Reaction equation

HRID 1931083 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][OH:8].[H-].[Na+].F[C:12]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:13]=1[C:14]#[N:15]>C1COCC1>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][O:8][C:12]1[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:23])[F:22])=[CH:16][C:13]=1[C:14]#[N:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5210162-Fluoro-5-(trifluoromethyl)benzonitrileHCID 643492(2S)-1-Methyl-2-pyrrolidinemethanol

Product 1

HCID 66643250(S)-2-((1-methylpyrrolidin-2-yl)methoxy)-5-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
22 °C

Procedure

To a solution of (S)-(1-methylpyrrolidin-2-yl)methanol (5.2 g, 45.1 mmol) in 25 mL of THF was added sodium hydride (1.970 g, 49.3 mmol). The reaction was stirred at 22° C. for 20 min. and 2-fluoro-5-(trifluoromethyl)benzonitrile (Aldrich) (8.54 g, 45.1 mmol) was added in 5 mL of THF. The reaction was stirred at 22° C. for 3 h. The solvent was evaporated under reduced pressure. The residue was dissolved in ether, washed with brine, water, dried with magnesium sulfate and concentrated to afford the title compound. MS (ESI) m/z 285 (M+H)+.

Workup

  1. stirringThe reaction was stirred at 22° C. for 3 h
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with brine, water
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f13aa2452aa54e98955ca7ae567972d7
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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