Ethylene Glycol → 7-Methyl 8-(phenylmethyl) 1,4-dioxa-8-azaspiro[4.5]decane-7,8-dicarboxylate

HRID 1196505Notes

Reaction equation

HRID 1196505 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH:4]([C:18]([O:20][CH3:21])=[O:19])[CH2:3]1.[CH2:22](O)[CH2:23][OH:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[O:24]1[C:2]2([CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[O:9])[CH:4]([C:18]([O:20][CH3:21])=[O:19])[CH2:3]2)[O:1][CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 15123243HCID 15123243, compound

Product 1

HCID 151232447-Methyl 8-(phenylmethyl) 1,4-dioxa-8-azaspiro[4.5]decane-7,8-dicarboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of the product of stage (ii) (5.06 g) and 1,2-ethanediol (1.06 ml) in benzene (100 ml) containing 4-toluenesulphonic acid (0.2 g) was stirred at reflux temperature under a Soxhlet cup filled with 4 Å molecular sieves for 4 h. The reaction mixture was allowed to cool to 22°, washed with 2N sodium carbonate (2×20 ml), water (20 ml) and dried. The benzene solution was evaporated in vacuo to give the title compound as an oil (5.75 g).

Workup

  1. temperatureat reflux temperature under a Soxhlet cup
  2. additionfilled with 4 Å molecular sieves for 4 h
  3. temperatureto cool to 22°
  4. washwashed with 2N sodium carbonate (2×20 ml), water (20 ml)
  5. customdried
  6. customThe benzene solution was evaporated in vacuo

Sources & evidence

ORD record
ord-99f86f930c8644cc83d7e4bb6efe370d
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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