Acetone → HCID 86736791, compound

HRID 2052345Notes

Reaction equation

HRID 2052345 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([O:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15]1)([C:8]1C=CC=CC=1)[C:2]1C=CC=CC=1.CS(O)(=O)=O.II.CC(C)=O>C(O)C.C(Cl)(Cl)Cl.C(OCC)(=O)C.O.[Pd]>[CH3:22][S:19]([OH:21])(=[O:20])=[O:18].[CH:1]([N:14]1[CH2:15][CH:16]([O:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH2:17]1)([CH3:8])[CH3:2]

Participants

8

Reactant 4

HCID 180AcetoneHCID 807IodineHCID 6395Methanesulfonic AcidHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 86736791HCID 86736791, compound

Reagents, catalysts & solvents 3

HCID 23219155Palladium hydrateCatalyst2×HCID 702EthanolSolventHCID 21584013Chloroform ethylacetateSolvent

Procedure

Hydrogenate a mixture of 1.0 mole 1-benzhydryl-3-methanesulfonyloxyazetidine, 1.0 mole methanesulfonic acid and 20% palladium hydroxide-on-carbon in ethyl alcohol at ca. 60 psi until the reaction is complete as shown by absence of the Compound IV using thin layer chromatography. (Silica gel GF plates are developed in chloroform:ethyl acetate (9:1) and visualized using iodine). Add additional 20% palladium hydroxide-on-carbon and acetone and continue the hydrogenation at ca. 60 psi for 5 days. Remove the catalyst by filtration and wash with ethanol. Remove the ethanol from the combined filtrates and washes by distillation at about 40° C. under reduced pressure and wash the residue with diethyl ether and air-dry to afford 1-isopropyl-3-methanesulfonyloxyazetidine methanesulfonate.

Workup

  1. customfor 5 days
  2. customRemove the catalyst
  3. filtrationby filtration
  4. washwash with ethanol
  5. customRemove the ethanol from the combined filtrates and washes
  6. distillationby distillation at about 40° C. under reduced pressure
  7. washwash the residue with diethyl ether
  8. customair-dry

Sources & evidence

ORD record
ord-9f8fcd7c27e14849919ff35f9c25f5db
Source dataset
uspto-grants-1980_01
Patent number
US04183923

Reaction notes

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