Methyl iodide → HCID 54317668, compound

HRID 376671Notes

Reaction equation

HRID 376671 reaction equation
[Li][CH:2](CC)C.C1CCCCC1.C(=O)=O.CC(C)=O.CN(CCN(C)C)C.[CH3:27][C:28]([N:31]([CH3:43])[C:32]1[CH:42]=[CH:41][CH:40]=[CH:39][C:33]=1[C:34]([NH:36][CH2:37][CH3:38])=[O:35])([CH3:30])[CH3:29].CI>C1COCC1.O>[CH2:37]([NH:36][C:34](=[O:35])[C:33]1[C:39]([CH3:2])=[CH:40][CH:41]=[CH:42][C:32]=1[N:31]([C:28]([CH3:29])([CH3:30])[CH3:27])[CH3:43])[CH3:38]

Participants

9

Reactant 6

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078CyclohexaneHCID 18522661Acetone cardiceHCID 54441024HCID 54441024, compoundHCID 178418400CID 53628100

Product 1

HCID 54317668HCID 54317668, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 1.3M s-BuLi in cyclohexane (9.8 mL, 12.8 mmol) was added dropwise to a dry-ice/acetone cooled solution of TMEDA (0.6 mL, 3.8 mmol) in THF (10 mL), followed by the dropwise addition of a solution of the compound of Example 188 (0.75 g, 3.2 mmol) in THF (5 mL). The reaction mixture was stirred at -78° C. for 30 min, then methyl iodide (2.3 g, 16 mol) was introduced in a single portion. This mixture was stirred for 2.5h at -78° C., then was warmed to -30° C., diluted with water, and extracted with EtOAc (2×). The combined organic extracts were dried (MgSO4), concentrated, and purified by HPLC with 1:4 EtOAc/cyclohexane to give 146 mg of the title compound as a light yellow solid, an 18% yield. m.p. 101°-103° C.

Workup

  1. temperaturewas warmed to -30° C.
  2. extractionextracted with EtOAc (2×)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by HPLC with 1:4 EtOAc/cyclohexane

Sources & evidence

ORD record
ord-f9a8c967abe546d288a6bc70519dda50
Source dataset
uspto-grants-2000_02
Patent number
USRE036562

Reaction notes

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