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

HRID 2175552Notes

Reaction equation

HRID 2175552 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-26f36a717b94495ba49cfa09f80105a0
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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