3,4-dihydro-2H-pyran → 1-(2-Tetrahydropyranyl)-4-[2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinone

HRID 67975Notes

Reaction equation

HRID 67975 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[NH:7][C:6](=[O:8])[CH2:5]1.[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.[OH2:15].[C:16]1(C)C=[CH:20][C:19](S(O)(=O)=O)=[CH:18][CH:17]=1>O1CCOCC1>[O:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[N:7]1[CH:4]([CH2:3][CH2:2][O:1][CH:20]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:5][C:6]1=[O:8]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 12769226HCID 12769226, compound

Product 1

HCID 143289841-(2-Tetrahydropyranyl)-4-[2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinoneYield 282.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Under nitrogen and at 25° C., a solution of 4-(2-hydroxyethyl)-2-azetidinone (62 mg, 0.539 mmole) in 0.5 ml of anhydrous p-dioxane is treated with 2,3-dihydropyran (0.98 ml, 1.08 mmoles) and p-toluenesulfonic acid monohydrate (19 mg, 0.10 mmole). The resulting solution is stirred for a period of 60 minutes and then partitioned between 10 ml of 0.5 M pH7 phosphate buffer and 10 ml of ethyl acetate. The aqueous phase is extracted a second time with ethyl acetate. The combined ethyl acetate solutions are washed with brine, dried over magnesium sulfate and filtered. The filtrate is evaporated under reduced pressure to give 215 mg of crude product. Purification by preparative thick-layer chromatography developing with ethyl acetate gives 80 mg of 1-(2-tetrahydropyranyl)-4-[2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinone as an oil.

Workup

  1. custompartitioned between 10 ml of 0.5 M pH7 phosphate buffer and 10 ml of ethyl acetate
  2. extractionThe aqueous phase is extracted a second time with ethyl acetate
  3. washThe combined ethyl acetate solutions are washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate is evaporated under reduced pressure
  7. customto give 215 mg of crude product
  8. customPurification by preparative thick-layer chromatography

Sources & evidence

ORD record
ord-42519362b28646ea9b70be29521e5ad1
Source dataset
uspto-grants-1982_08
Patent number
US04347367

Reaction notes

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