1-(Azetidin-1-yl)-2-[4-(benzyloxy)-2-chlorophenyl]ethanone → 1-(Azetidin-1-yl)-2-(2-chloro-4-hydroxyphenyl)ethanone

HRID 1474676Notes

Reaction equation

HRID 1474676 reaction equation
[N:1]1([C:5](=[O:22])[CH2:6][C:7]2[CH:12]=[CH:11][C:10]([O:13]CC3C=CC=CC=3)=[CH:9][C:8]=2[Cl:21])[CH2:4][CH2:3][CH2:2]1>C(O)C.[OH-].[OH-].[Pd+2]>[N:1]1([C:5](=[O:22])[CH2:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=2[Cl:21])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 867111801-(Azetidin-1-yl)-2-[4-(benzyloxy)-2-chlorophenyl]ethanone

Product 1

HCID 708188251-(Azetidin-1-yl)-2-(2-chloro-4-hydroxyphenyl)ethanone

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

1-(azetidin-1-yl)-2-[4-(benzyloxy)-2-chlorophenyl]ethanone (520 mg, 1.65 mmol) was dissolved in ethanol (2 ml) and palladium hydroxide on carbon (20%) (116 mg, 0.165 mmol) added. The mixture was stirred under an atmosphere of hydrogen gas at RT overnight. The mixture was filtered and the filtrate concentrated under reduced pressure. The reside was purified by column chromatography using a Biotage RP C18 cartridge (30 g) using a gradient eluant of 10-100% water:acetonitrile+0.05% formic acid. to afford the title compound. LC/MS (m/z): 226 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe reside was purified by column chromatography

Sources & evidence

ORD record
ord-553360fd949e469db9fc3a65b96c46d2
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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