Succinimide → 1-(1,4-Dioxaspiro[4.5]decan-8-yl)pyrrolidine-2,5-dione

HRID 1896872Notes

Reaction equation

HRID 1896872 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C:2]1=[O:7].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[O:18]1[C:22]2([CH2:27][CH2:26][C:25](C3C(O)=CC=CN=3)=[CH:24][CH2:23]2)[O:21][CH2:20][CH2:19]1>CN(C=O)C>[O:18]1[C:22]2([CH2:27][CH2:26][CH:25]([N:1]3[C:5](=[O:6])[CH2:4][CH2:3][C:2]3=[O:7])[CH2:24][CH2:23]2)[O:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 11439SuccinimideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 585625152-(1,4-Dioxa-spiro[4.5]dec-7-en-8-yl)-pyridin-3-ol

Product 1

HCID 585627101-(1,4-Dioxaspiro[4.5]decan-8-yl)pyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of pyrrolidine-2,5-dione (210 mg, 2 mmol) in DMF was treated with sodiumhexamethyldisilazid (1.5 eq), stirred for 30 min and treated with 4-dioxaspiro[4.5]decan-8-yl methanesulfonate (250 mg, 1 mmol) from example 1, step A, 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-179cad7f78bf482fa1986215754e7b14
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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