Tetrahydrofuran → HCID 19799613, compound

HRID 974645Notes

Reaction equation

HRID 974645 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][CH:7]1[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]1.[C:19](=[O:22])([O-:21])[O-].[K+].[K+].[N:25]12[CH2:33][CH2:32][CH2:31][CH:30]1[CH2:29][NH:28][CH2:27][CH2:26]2.[O:34]1CCCC1>O>[C:5]([OH:34])(=[O:6])/[CH:14]=[CH:15]/[C:19]([OH:21])=[O:22].[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][CH:7]1[CH2:10][N:9]([C:11]([N:28]2[CH2:27][CH2:26][N:25]3[CH2:33][CH2:32][CH2:31][CH:30]3[CH2:29]2)=[O:12])[CH2:8]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 558578Octahydropyrrolo(1,2-a)pyrazineHCID 197996061-Chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine

Product 1

HCID 19799613HCID 19799613, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.8 g (0.01 mole) of 3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride in 20 ml of tetrahydrofuran was stirred with 1.4 g (0.01 mole) of potassium carbonate then treated with the dropwise addition of 1.3 g (0.01 mole) of 1,4-diazabicyclo(4.3.0)nonane. After stirring for 30 minutes, approximately 2 g of ice was added and stirring continued for 64 hr. The reaction mixture was diluted with 200 ml of water and the oil which separated was extracted into methylene chloride (2×50 ml), dried over magnesium sulfate and concentrated in vacuo to a pale yellow oil (3.9 g). This oil was placed in 25 ml of isopropanol and treated with 1.2 g of fumaric acid and heated to give a clear solution. The solvent was removed in vacuo and the residue crystallized on standing. The residue was recrystallized from ethyl acetate with 5% isopropyl ether and from methyl isobutyl ketone to yield 2.5 g (51.5%) of beige colored crystals, m.p. 102°-110° C.

Workup

  1. stirringstirring
  2. waitcontinued for 64 hr
  3. customthe oil which separated
  4. extractionwas extracted into methylene chloride (2×50 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo to a pale yellow oil (3.9 g)
  7. additiontreated with 1.2 g of fumaric acid
  8. temperatureheated
  9. customto give a clear solution
  10. customThe solvent was removed in vacuo
  11. customthe residue crystallized
  12. customThe residue was recrystallized from ethyl acetate with 5% isopropyl ether and from methyl isobutyl ketone

Sources & evidence

ORD record
ord-1f019d307b1a40a190b85d1db04989ec
Source dataset
uspto-grants-1991_11
Patent number
US05068231

Reaction notes

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