1-(Diphenylmethyl)-3-phenylazetidine → 3-Phenylazetidine

HRID 1013116Notes

Reaction equation

HRID 1013116 reaction equation
C([N:14]1[CH2:17][CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].C(O)C>[C:18]1([CH:16]2[CH2:17][NH:14][CH2:15]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 160894471-(Diphenylmethyl)-3-phenylazetidineHCID 178418361HCID 178418361, compound

Product 1

HCID 289015863-PhenylazetidineYield 34%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent2×

Procedure

Add 20% palladium hydroxide on activated carbon (0.130 g) and ethanol (25 mL) to a Parr pressure vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (400 kPa), seal the vessel and agitate the mixture at RT for 15 min. Vent the hydrogen from the reaction vessel and purge the reaction vessel with nitrogen. Add 1-benzhydryl-3-phenylazetidine (0.515 g, 0.00172 mol) and ethanol (75 mL) to the pressure vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (400 kPa), seal the vessel and agitate the reaction at RT for 20 h. Turn off the agitation, vent the excess hydrogen from the vessel, purge the vessel with nitrogen and filter the reaction mixture to remove the palladium on carbon catalyst. Concentrate and purify (silica gel chromatography, eluting with 5:95 to 10:90 2 M ammonia in methanol:DCM) to give the title compound (76 mg, 34%).

Workup

  1. customPurge the reaction vessel with nitrogen
  2. customseal the vessel
  3. custompurge the reaction vessel with nitrogen
  4. customPurge the reaction vessel with nitrogen
  5. customseal the vessel
  6. stirringagitate
  7. customthe reaction at RT for 20 h
  8. custompurge the vessel with nitrogen
  9. filtrationfilter the reaction mixture
  10. customto remove the palladium on carbon catalyst
  11. concentrationConcentrate
  12. custompurify
  13. wash(silica gel chromatography, eluting with 5:95 to 10:90 2 M ammonia in methanol:DCM)

Sources & evidence

ORD record
ord-79662dc2a31f404cb9b2129b40f3d664
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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