Methyl iodide → HCID 11644978, compound

HRID 916347Notes

Reaction equation

HRID 916347 reaction equation
[O:1]=[C:2]1[CH2:8][CH:7]2[N:9]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]([C:20]#[N:21])=[CH:12][CH:11]=3)[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.[CH3:22][Si]([N-][Si](C)(C)C)(C)C.[Li+].IC>C1COCC1>[CH3:22][CH:8]1[C:2](=[O:1])[CH2:3][CH:4]2[N:9]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]([C:20]#[N:21])=[CH:12][CH:11]=3)[CH:7]1[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 247436404-(3-Oxo-8-azabicyclo[3.2.1]octan-8-yl)naphthalene-1-carbonitrile

Product 1

HCID 11644978HCID 11644978, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 156AF03-217 (552 mg, 2 mmol) in THF (20 mL) under argon atmosphere at −78° C. was added dropwise lithium bis(trimethylsilyl)amide (2.6 mL, 2.6 mmol, 1 M in THF). After 30 min at −78° C., iodomethane (2.0 mL) was added over 1 min and the reaction was allowed to warm to rt overnight. Partitioning of the reaction mixture between ethyl acetate (2×500 mL) and water (500 mL), drying of the combined organic phases over Na2SO4, filtration, removing of volatiles in vacuo and purification by preparative TLC (ethyl acetate/n-heptane 1:4, 5× eluted) afforded the title compound (115 mg, 20%) as a thick oil.

Workup

  1. customPartitioning of the reaction mixture between ethyl acetate (2×500 mL) and water (500 mL)
  2. dry with materialdrying of the combined organic phases over Na2SO4, filtration
  3. customremoving of volatiles in vacuo and purification by preparative TLC (ethyl acetate/n-heptane 1:4, 5× eluted)

Sources & evidence

ORD record
ord-27e89e45ffd949da9e8f56773ad492c6
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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