Methyl iodide → HCID 57424233, compound

HRID 2377373Notes

Reaction equation

HRID 2377373 reaction equation
[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[CH:10]=2)[C:5](=O)[CH2:4][CH2:3]1.[CH:22]1([NH2:25])[CH2:24][CH2:23]1.[C:26]([BH3-])#N.[Na+].C(=O)([O-])[O-].[K+].[K+].CI>ClCCl.O.C(=O)([O-])[O-].[Na+].[Na+].C(O)(=O)C.C(#N)C>[CH:22]1([N:25]([CH3:26])[CH:5]2[CH2:4][CH2:3][C:2]([CH3:21])([CH3:1])[C:11]3[CH:10]=[C:9]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:14])=[O:15])[CH:8]=[CH:7][C:6]2=3)[CH2:24][CH2:23]1

Participants

11

Reactant 5

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 225687874,4-Dimethyl-6-trifluoromethylsulfonyloxy-1,2,3,4-tetrahydronaphthalene-1-one

Product 1

HCID 57424233HCID 57424233, compoundYield 87%

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 4,4-dimethyl-6-trifluoromethylsulfonyloxy-1,2,3,4-tetrahydronaphthalene-1-one (U.S. Pat. No. 6,252,090, 0.85 g, 2.64 mmol) in dichloromethane (6 mL) and acetonitrile (3 mL) was treated with cyclopropyl amine (3 mL, 43.4 mmol). After 5 minutes, acetic acid (3 mL) was added followed by sodium cyanoborohydride (0.66 g, 10.55 mmol). The reaction was stirred overnight at ambient temperature. It was then diluted with water and saturated aqueous sodium carbonate solution and extracted with ethyl acetate. The combined organic extract was washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil. The oil was dissolved in acetone (20 mL) and treated with potassium carbonate (1.08 g, 7.8 mmol) and methyl iodide (1.6 mL, 26 mmol). The resulting reaction mixture was stirred at ambient temperature overnight. The solids were filtered off, the filtrate was evaporated in vacuo and the residue was subjected to flash column chromatography over silica gel (230-400 mesh) to afford the title compound (0.85 g, 87%) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe combined organic extract
  3. washwas washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to an oil
  7. dissolutionThe oil was dissolved in acetone (20 mL)
  8. customThe resulting reaction mixture
  9. stirringwas stirred at ambient temperature overnight
  10. filtrationThe solids were filtered off
  11. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-13311609a43844ca853d828d6a43a293
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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