2-Pyrrolidone → 1-(1,4-Dioxaspiro[4.5]decan-8-yl)pyrrolidin-2-one

HRID 1896856Notes

Reaction equation

HRID 1896856 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[H-].[Na+].CS(O[CH:14]1[CH2:23][CH2:22][C:17]2([O:21][CH2:20][CH2:19][O:18]2)[CH2:16][CH2:15]1)(=O)=O>CN(C=O)C>[O:18]1[C:17]2([CH2:22][CH2:23][CH:14]([N:1]3[CH2:5][CH2:4][CH2:3][C:2]3=[O:6])[CH2:15][CH2:16]2)[O:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 149667411,4-Dioxaspiro(4.5)decan-8-yl methanesulfonate

Product 1

HCID 109002931-(1,4-Dioxaspiro[4.5]decan-8-yl)pyrrolidin-2-oneYield 11.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Pyrrolidin-2-one (720 mg, 8.46 mmol) in DMF (5 mL) was treated with NaH (203 mg, 8.46 mmol) at room temperature. The mixture allowed to stir for 30 min. 1,4-dioxaspiro[4.5]decan-8-yl methanesulfonate (500 mg, 2.12 mmol) from above step A, in DMF (3 mL) was added to the mixture and stirred at 130° C. for 3 h. The mixture was cooled to room temperature, quenched with NH4Cl, and extracted into EtOAc. Washed the EtOAc layer with saturated NaCl, dried over Na2SO4 and evaporated. Purified by silica prep TLC to give 55 mg (11.5%) of 1-(1,4-dioxaspiro[4.5]decan-8-yl)pyrrolidin-2-one.

Workup

  1. stirringstirred at 130° C. for 3 h
  2. customquenched with NH4Cl
  3. extractionextracted into EtOAc
  4. washWashed the EtOAc layer with saturated NaCl
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customPurified by silica prep TLC

Sources & evidence

ORD record
ord-2ce2d8c96c8d4a18932ee09386df8c9e
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

Loading…