Trityl chloride → 1-[3-(Trityloxy)-1-azetidinyl]-1-ethanone

HRID 2377182Notes

Reaction equation

HRID 2377182 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6](=[O:8])[CH3:7])[CH2:3]1.N12CCCN=C1CCCCC2.[C:20](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:20]([O:1][CH:2]1[CH2:5][N:4]([C:6](=[O:8])[CH3:7])[CH2:3]1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 110623451-(3-Hydroxyazetidin-1-yl)ethan-1-one

Product 1

HCID 219901691-[3-(Trityloxy)-1-azetidinyl]-1-ethanoneYield 69.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 50 mL of methylene chloride was dissolved 10.0 g of 1-(3-hydroxy-1-azetidinyl)-1-ethanone, and 31.2 mL of 1,8-diazabicyclo[5,4,0]undec-7-ene and 29.1 g of trityl chloride were added thereto under ice-cooling, after which the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 100 mL of ice water and the organic layer was separated. The organic layer was washed with diluted hydrochloric acid, water and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. Diisopropyl ether was added to the residue and the crystals precipitated were collected by filtration to obtain 21.7 g of 1-[3-(trityloxy)-1-azetidinyl]-1-ethanone as light-yellow crystals.

Workup

  1. additionwere added
  2. temperatureunder ice-cooling
  3. customthe organic layer was separated
  4. washThe organic layer was washed with diluted hydrochloric acid, water
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. additionDiisopropyl ether was added to the residue
  9. customthe crystals precipitated
  10. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-f6571c45d6914c1d98565317ee92e6c5
Source dataset
uspto-grants-2008_12
Patent number
US07468443B2

Reaction notes

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