Water → 2-Azaspiro[4.5]decane-3,8-dione

HRID 2099692Notes

Reaction equation

HRID 2099692 reaction equation
O1[C:5]2([CH2:15][CH2:14][C:8]3([CH2:12][C:11](=[O:13])[NH:10][CH2:9]3)[CH2:7][CH2:6]2)[O:4]CC1.O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O>[CH2:9]1[C:8]2([CH2:7][CH2:6][C:5](=[O:4])[CH2:15][CH2:14]2)[CH2:12][C:11](=[O:13])[NH:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 577954141,4-Dioxa-10-azadispiro[4.2.4^{8}.2^{5}]tetradecan-11-one

Product 1

HCID 577955102-Azaspiro[4.5]decane-3,8-dioneYield 58%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-11-one (3.95 g, 18.7 mmol) in 160 mL of acetone was added 16 mL of water and pyridinium p-toluenesulfonate (1.41 g, 5.61 mmol). The resulting mixture was stirred at reflux for 20 h. Then, it was cooled and concentrated. The crude was purified by silica gel column chromatography using a 5% MeOH:EtOAc mixture as eluent to afford 2-aza-spiro[4.5]decane-3,8-dione (1.80 g, 58%) as a white solid.

Workup

  1. temperatureat reflux for 20 h
  2. temperatureThen, it was cooled
  3. concentrationconcentrated
  4. customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ec403a407a7e4a1c9372b04caef70c72
Source dataset
uspto-grants-2009_08
Patent number
US07569600B2

Reaction notes

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