Methyl iodide → HCID 21075141, compound

HRID 1374245Notes

Reaction equation

HRID 1374245 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

Preparation C6, Step 1. 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-1b93b2a0a5014f76a6dee9e9154e2409
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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