Triethylamine → 8-(Methanesulfonyl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 1636181Notes

Reaction equation

HRID 1636181 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]1[O:15][C:9]2([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[O:8][CH2:7]1.C(N(CC)CC)C>CCOCC>[CH2:6]1[O:15][C:9]2([CH2:14][CH2:13][N:12]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:11][CH2:10]2)[O:8][CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 674351,4-Dioxa-8-azaspiro(4.5)decane

Product 1

HCID 173779138-(Methanesulfonyl)-1,4-dioxa-8-azaspiro[4.5]decaneYield 95.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methanesulphonyl chloride (24.8 g, 0.217mol) was added dropwise to a solution of 4-piperidone ethylene ketal (28.2 g, 0.197 mol) and triethylamine (30.2 ml, 0.217 mol) in ether (280 ml), and the reaction stirred at room temperature for 3 hours. The mixture was washed consecutively with water (2×), hydrochloric acid (1N), and saturated sodium bicarbonate solution, dried (MgSO4), filtered and evaporated in vacuo. The residue was triturated with hexane, filtered and dried to give the desired product as an off-white solid (41.6 g, 95%).

Workup

  1. washThe mixture was washed consecutively with water (2×), hydrochloric acid (1N), and saturated sodium bicarbonate solution
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was triturated with hexane
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-0f01e2f79bae4f63b010c44d195eb930
Source dataset
uspto-grants-2003_01
Patent number
US06511993B1

Reaction notes

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