Methyl iodide → HCID 59541862, compound

HRID 2388324Notes

Reaction equation

HRID 2388324 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:12]=[CH:13][C:14](=[O:17])[NH:15][CH:16]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[C:18]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([C:11]3[CH:12]=[CH:13][C:14](=[O:17])[N:15]([CH3:18])[CH:16]=3)[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1.[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[N:15][CH:16]=3)[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 59541792HCID 59541792, compound

Product 2

HCID 59541862HCID 59541862, compoundHCID 66750189HCID 66750189, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 5-(1,4-dioxa-spiro[4.5]dec-8-yl)-1H-pyridin-2-one (as prepared in the previous step, 750 mg, 3.19 mmol) in DMF (5 mL) was treated with Cs2CO3 (Aldrich, 1.56 g, 4.80 mmol) at room temperature for 10 min. MeI (Aldrich, 330 μL, 4.80 mmol) was added into the reaction solution and heated at 70° C. for 6 hours. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give yellow oil, which was then purified by silica gel column on a CombiFlash® system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as a white solid along with O-alylated product, 5-(1,4-dioxa-spiro[4.5]dec-8-yl)-2-methoxy-pyridine.

Workup

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give yellow oil, which
  7. customwas then purified by silica gel column on a CombiFlash® system

Sources & evidence

ORD record
ord-d27253f9137344a4804439e4ce8ceb55
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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