Diphenylmethane → Methyl azetidin-3-yl(3,5-difluorophenyl)acetate

HRID 602675Notes

Reaction equation

HRID 602675 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[C:14]2[CH2:17][N:16](C(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:15]2)[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.C1(CC2C=CC=CC=2)C=CC=CC=1>CO.Cl.CCOCC.[Pd]>[NH:16]1[CH2:17][CH:14]([CH:9]([C:4]2[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=2)[C:10]([O:12][CH3:13])=[O:11])[CH2:15]1

Participants

7

Reactant 2

HCID 7580DiphenylmethaneHCID 57559921Methyl (3,5-difluorophenyl)[1-(diphenylmethyl)azetidin-3-ylidene]acetate

Product 1

HCID 67065947Methyl azetidin-3-yl(3,5-difluorophenyl)acetate

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.406 g (1 mmol) of methyl (3,5-difluorophenyl)[1-(diphenylmethyl)azetidin-3-ylidene]acetate and 25 mg of 10% Pd/C in 10 mL of methanol and 1 mL of 1M HCl in ether was shaken under 40 psi H2 for 18 h. The mixture was filtered through CELITE and the solid residue was washed with 30 mL of methanol. The filtrate was concentrated to afford a mixture of the title compound and diphenylmethane, which was not separated but was used directly in the next step; Mass Spectrum: m/e=242 (M+1).

Workup

  1. filtrationThe mixture was filtered through CELITE
  2. washthe solid residue was washed with 30 mL of methanol
  3. concentrationThe filtrate was concentrated
  4. customto afford

Sources & evidence

ORD record
ord-52320e0fb63a4947981f667110b2b7cf
Source dataset
uspto-grants-2011_03
Patent number
US07906503B2

Reaction notes

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