Ethylene Glycol → Ethyl 8-(4-chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decane-7-carboxylate

HRID 15744Notes

Reaction equation

HRID 15744 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:16]([CH2:17][CH3:18])[CH2:15][C:14](=[O:19])[CH2:13][CH:12]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[Si](Cl)(C)C.[CH2:30](O)[CH2:31][OH:32]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:16]([CH2:17][CH3:18])[CH2:15][C:14]3([O:32][CH2:31][CH2:30][O:19]3)[CH2:13][CH:12]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6397ChlorotrimethylsilaneHCID 59342392Ethyl 1-(4-chlorophenylsulfonyl)-6-ethyl-4-oxopiperidine-2-carboxylate

Product 1

HCID 59342412Ethyl 8-(4-chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decane-7-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 1-(4-chlorophenylsulfonyl)-6-ethyl-4-oxopiperidine-2-carboxylate (109; 5.31 g, 14.2 mmol), TMSCl (5.41 ml, 42.6 mmol), and ethylene glycol (3.96 ml, 71.0 mmol) were added to CH2Cl2 (50 ml) and refluxed under nitrogen for 3 hours. The reaction mixture was concentrated tinder reduced pressure, and taken up in equal portions of EtOAc and water. The aqueous layer was washed with several more portions of EtOAc, dried over Na2SO4, and concentrated to give 5.67 g (96%) of a mixture of cis/trans (4:96) isomers as a clear oil which solidified upon standing. The material was used without further purification.

Workup

  1. temperaturerefluxed under nitrogen for 3 hours
  2. concentrationThe reaction mixture was concentrated tinder reduced pressure
  3. washThe aqueous layer was washed with several more portions of EtOAc
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6d0500193c3c4b7c849472d7a03109d1
Source dataset
uspto-grants-2010_06
Patent number
US07732609B2

Reaction notes

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