Methyl iodide → HCID 21075141, compound

HRID 1171471Notes

Reaction equation

HRID 1171471 reaction equation
[C:1]12([C:11]3[CH:15]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:21][Si]([N-][Si](C)(C)C)(C)C.[K+].IC.C(OCC)(=O)C>C1COCC1>[C:1]12([C:11]3[CH:15]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:13]([CH3:21])[CH:12]=3)[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

6

Reactant 4

HCID 6328Methyl iodide2×HCID 8857Ethyl AcetateHCID 3251421Potassium bis(trimethylsilyl)amide2×HCID 21075142HCID 21075142, compound

Product 1

HCID 21075141HCID 21075141, compoundYield 298.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-(adamant-1-yl)-pyrrole-5-carboxylate (0.20 g, 0.7 mmol, 1 eq) was dissolved in THF (20 mL). Potassium bis(trimethylsilyl)amide (0.5 M in Tol, 1.62 mL, 0.81 mmol, 1.1 eq) was added thereto followed by iodomethane (0.102 mL, 1.6 mmol, 2.2 eq). The next day, the same amounts of potassium bis(trimethylsilyl)amide and iodomethane were again added to drive the reaction to completion. In 4 h, the reaction was finished. Ethyl acetate was added (100 mL) and the organic layer was washed with water (2×), brine, dried (MgSO4) and stripped to yield 600 mg of ethyl 3-(adamant-1-yl)-1-methylpyrrole-5-carboxylate, which was used as is in the next step. MS found: (M+H)+=288.16.

Workup

  1. customthe reaction to completion
  2. washthe organic layer was washed with water (2×), brine
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-90154dbd52cc4a13b0eb4a04f7fc6610
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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