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

HRID 981852Notes

Reaction equation

HRID 981852 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-toluene sulfonic 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 pH 7 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 216 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 0.5M pH 7 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 216 mg of crude product
  8. customPurification by preparative thick-layer chromatography

Sources & evidence

ORD record
ord-e4121f85e11645b5bedc302d74bcb2f4
Source dataset
uspto-grants-1991_02
Patent number
US04992542

Reaction notes

Loading…