Dimethylformamide → HCID 66750739, compound

HRID 2388340Notes

Reaction equation

HRID 2388340 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3C(O)=N[CH:14]=[CH:15][CH:16]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].CI.C(=O)(O)[O-:27].[Na+].[CH3:31][N:32](C=O)[CH3:33]>>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([C:11]3[N:32]([CH3:33])[CH:31]=[CH:14][C:15](=[O:27])[CH:16]=3)[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 178517702HCID 178517702, compound

Product 1

HCID 66750739HCID 66750739, compound

Procedure

To a mixture of 3-(1,4-Dioxa-spiro[4.5]dec-8-yl)-pyridin-2-ol (as prepared in example 10, Step B, 182 mg, 0.774 mmol) in dry DMF (5 mL) was added cesium carbonate (367 mg, 1.13 mmol) and methyl iodide (80 μL, 1.28 mmol). The reaction mixture was stirred at room temperature for 16 hours, poured onto saturated sodium bicarbonate solution and extracted with ethyl acetate. Purification by flash chromatography (SiO2, 0-10% MeOH/CH2Cl2) afforded 2-(1,4-dioxa-spiro[4.5]dec-8-yl)-1-methyl-1H-pyridin-4-one as the more polar material along with the O-Methyl isomer as the less polar isomer.

Workup

  1. extractionextracted with ethyl acetate
  2. customPurification by flash chromatography (SiO2, 0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-b54c965e8d40458c85847e9b2204bed1
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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