Methyl iodide → tert-Butyl methyl-(3-tri-n-butylstannylcyclopent-2-enyl)carbamate

HRID 17622

Reaction equation

HRID 17622 reaction equation
[CH2:1]([Sn:5]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:19][CH2:20][CH2:21][CH3:22])[C:6]1[CH2:10][CH2:9][CH:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH3:27]I.[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH3:27][N:11]([CH:8]1[CH2:9][CH2:10][C:6]([Sn:5]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:23][CH2:24][CH2:25][CH3:26])=[CH:7]1)[C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 15630117Tert-butyl (3-tri-n-butylstannylcyclopent-2-enyl)carbamate

Product 1

HCID 68584969tert-Butyl methyl-(3-tri-n-butylstannylcyclopent-2-enyl)carbamateYield 96.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tert-butyl (3-tri-n-butylstannylcyclopent-2-enyl)carbamate (2.0 g, 4.24 mmol) was dissolved in N,N-dimethylformamide (40 ml), and at 0° C., methyl iodide (527 μl, 8.47 mmol) and then sodium hydride (55%, w/w), (277 mg, 6.35 mmol) were added. With gradually warming from 0° C. up to room temperature, this was stirred for 24 hours. At 0° C., aqueous saturated ammonium chloride solution was added to the solution, followed by stirring at the same temperature for 30 minutes. The solution was extracted three times with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=99:1, v/v) to obtain a colorless oil (1.982 g, 96%).

Workup

  1. temperatureWith gradually warming from 0° C. up to room temperature
  2. stirringby stirring at the same temperature for 30 minutes
  3. extractionThe solution was extracted three times with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away
  8. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

Sources & evidence

ORD record
ord-6e43b11caf5d4fa8a96eac542119e500
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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