Methyl iodide → HCID 21075141, compound

HRID 1455343Notes

Reaction equation

HRID 1455343 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-2a8fee93c8c64430aee58b53f85d41c7
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

Loading…