Methyl iodide → HCID 131727093, compound

HRID 2115599Notes

Reaction equation

HRID 2115599 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:22])([CH3:21])[CH:8]1[CH2:12][N:11]([CH:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:10](=[O:20])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:23][Si]([N-][Si](C)(C)C)(C)C.[Li+].CI>O1CCCC1>[C:1]([SiH2:5][O:6][C:7]([CH3:22])([CH3:21])[CH:8]1[CH2:12][N:11]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[C:10](=[O:20])[CH:9]1[CH3:23])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 1317270924-(Tert-butyl-dimethyl-silanyloxymethyl)-1-cycloheptyl-pyrrolidine-2-one

Product 1

HCID 131727093HCID 131727093, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of Example 1B (1.09 g, 3.07 mmoles) in tetrahydrofuran (3.5 mL) was added drop wise to a solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (3.7 mL, 3.7 mmoles) at room temperature and stirred for two hours at that temperature. A solution of methyl iodide (0.54 g, 3.83 mmoles) in tetrahydrofuran (1 mL) was added drop wise to the reaction mixture at room temperature and stirred for another two hours. The reaction was quenched with 10% NH4Cl (25 mL) and extracted with ethyl acetate. The organic layer was washed with brine (25 mL), dried with MgSO4, filtered, and solvent evaporated in vacuo. The crude product was purified by flash column chromatography (hexanes:ethyl acetate 95:5 to 60:40) to provide the title compound.

Workup

  1. stirringstirred for another two hours
  2. customThe reaction was quenched with 10% NH4Cl (25 mL)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine (25 mL)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customsolvent evaporated in vacuo
  8. customThe crude product was purified by flash column chromatography (hexanes:ethyl acetate 95:5 to 60:40)

Sources & evidence

ORD record
ord-ca388d374f254606816cd1c89170cd96
Source dataset
uspto-grants-2008_10
Patent number
US07435833B2

Reaction notes

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