Water → HCID 67508958, compound

HRID 623426Notes

Reaction equation

HRID 623426 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH:8]([C:10]1[CH:11]=[N:12][C:13]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[CH:14][CH:15]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:26].O>CN(C)C=O>[CH3:26][N:7]([CH:8]([C:10]1[CH:11]=[N:12][C:13]([O:16][CH2:17][C:18]([F:19])([F:20])[F:21])=[CH:14][CH:15]=1)[CH3:9])[C:6](=[O:22])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 131735178HCID 131735178, compound

Product 1

HCID 67508958HCID 67508958, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of tert-butyl(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)carbamate (221 mg, 0.69 mmol, Step-1, single enantiomer) and sodium hydride (61 mg, 1.52 mmol, 60% in oil) in N,N-dimethylformamide (7 mL) is added dropwise iodomethane (0.065 mL, 1.04 mL) at room temperature. After stirring at room temperature for 3.5 hours, the reaction mixture is slowly poured into water (30 mL) and extracted with ethyl acetate (30 mL). The organic layer is washed with water (30 mL) and dried over sodium sulfate. After concentration in vacuo, the residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (9:1) to give 198 mg (86% yield) of the title compound as colorless oil.

Workup

  1. extractionextracted with ethyl acetate (30 mL)
  2. washThe organic layer is washed with water (30 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationAfter concentration in vacuo
  5. customthe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-98f405e09883428497f6d9178dca4326
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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