Dimethylformamide → HCID 117932987, compound

HRID 1477611Notes

Reaction equation

HRID 1477611 reaction equation
[CH3:1]N(C)C=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14]2)=[CH:9][CH:8]=1.[H-].[Na+].CI>C(OCC)(=O)C>[F:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:17][CH2:16][CH:15]([N:18]([CH3:1])[C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[CH2:14]2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 58975132HCID 58975132, compound

Product 1

HCID 117932987HCID 117932987, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an N,N-dimethylformamide solution (3.9 mL) of tert-butyl [1-(4-fluorophenyl)pyrrolidin-3-yl]carbamate (195 mg, 0.70 mmol) synthesized in Reference Synthesis Example 79, sodium hydride (28 mg, 0.70 mmol, purity 60%) and methyl iodide (44 μL, 0.70 mmol) were added at 0° C. and the resultant solution was stirred at room temperature for 1 day. To the reaction solution, the same amounts of sodium hydride and methyl iodide were further added and the resultant mixture was stirred for 1 day. After completion of the reaction, ethyl acetate was added to the reaction solution and the resultant mixture was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel (amino-based) column chromatography (hexane/ethyl acetate=9/1) to obtain the title compound (181 mg, yield 88%).

Workup

  1. additionwere added at 0° C.
  2. additionwas added to the reaction solution
  3. washthe resultant mixture was washed with water and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel (amino-based) column chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-12027348f5d74d16b4083d5a339e4077
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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