D-Psicose → Ethyl 3-(1-azetidin-3-yl-2-fluoro-2-methylpropyl)-5-fluorobenzoate

HRID 602986Notes

Reaction equation

HRID 602986 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([CH:12]([C:17]3[CH:18]=[C:19]([CH:25]=[C:26]([F:28])[CH:27]=3)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:13]([F:16])([CH3:15])[CH3:14])[CH2:9]2)C=CC=CC=1.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O.[H][H]>CCO.[OH-].[OH-].[Pd+2]>[NH:8]1[CH2:11][CH:10]([CH:12]([C:17]2[CH:18]=[C:19]([CH:25]=[C:26]([F:28])[CH:27]=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:13]([F:16])([CH3:15])[CH3:14])[CH2:9]1

Participants

6

Reactant 3

HCID 441036D-PsicoseHCID 67055389Ethyl 3-{1-[1-(diphenylmethyl)azetidin-3-yl]-2-fluoro-2-methylpropyl}-5-fluorobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 67055353Ethyl 3-(1-azetidin-3-yl-2-fluoro-2-methylpropyl)-5-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Ethyl 3-{1-[1-(diphenylmethyl)azetidin-3-yl]-2-fluoro-2-methylpropyl}-5-fluorobenzoate (7.6 g, 16.40 mmol) was hydrogenated in 150 mL of EtOH in the presence 3.4 g of Pd(OH)2 under 50 Psi pressure hydrogen for 24 h. Then it was filtered to remove the solid and washed with CH2Cl2. The combined organic layer was concentrated and washed with hexanes/ether to afford the title compound as an white solid. Mass Spectrum: m/e=298 (M+1).

Workup

  1. filtrationThen it was filtered
  2. customto remove the solid
  3. washwashed with CH2Cl2
  4. concentrationThe combined organic layer was concentrated
  5. washwashed with hexanes/ether

Sources & evidence

ORD record
ord-126d44dabe954a5eb55db340fb839529
Source dataset
uspto-grants-2011_03
Patent number
US07906652B2

Reaction notes

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