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

HRID 867574Notes

Reaction equation

HRID 867574 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.O.[C:16]1(C)C=[CH:20][C:19](S(O)(=O)=O)=[CH:18][CH:17]=1.C(OCC)(=[O:29])C>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:29]2)[CH2:5][C:6]1=[O:8]

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 12769226HCID 12769226, compound

Product 1

HCID 143289841-(2-Tetrahydropyranyl)-4-[2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinone

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 0.5M 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 unnder reduced pressure to give 216 mg of crude product. Purification by preparation thick-layer chromtography 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 0.5M 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 unnder reduced pressure
  7. customto give 216 mg of crude product
  8. customPurification
  9. customby preparation thick-layer chromtography

Sources & evidence

ORD record
ord-3987929bf8284584bb3498924706805a
Source dataset
uspto-grants-1988_10
Patent number
US04775669

Reaction notes

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