2-Pyridone → 1-(1,4-dioxaspiro[4.5]decan-8-yl)pyridin-2(1H)-one

HRID 1896870Notes

Reaction equation

HRID 1896870 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](C3C(O)=CC=CN=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[NH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]1=[O:24].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([N:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]3=[O:24])[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 88712-PyridoneHCID 10796Cesium carbonateHCID 585625152-(1,4-Dioxa-spiro[4.5]dec-7-en-8-yl)-pyridin-3-ol

Product 1

HCID 585629001-(1,4-dioxaspiro[4.5]decan-8-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-dioxaspiro[4.5]decan-8-yl methanesulfonate (497 mg, 2 mmol) from example 1, step A and pyridin-2(1H)-one (200 mg, 2 mmol) in DMF was treated with Cs2CO3 (1 g, 3 mmol) and heated at 80° C. for 18 h. DMF was removed under vacuum and the residue was purified by silica column chromatography to give the title compound.

Workup

  1. customDMF was removed under vacuum
  2. customthe residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-2fb725ec3c08427f9de11f34617a3c8a
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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