1-(Azetidin-1-yl)-2-[4-(benzyloxy)-2-methoxyphenyl]ethanone → 1-(Azetidin-1-yl)-2-(4-hydroxy-2-methoxyphenyl)ethanone

HRID 1474686Notes

Reaction equation

HRID 1474686 reaction equation
[N:1]1([C:5](=[O:23])[CH2:6][C:7]2[CH:12]=[CH:11][C:10]([O:13]CC3C=CC=CC=3)=[CH:9][C:8]=2[O:21][CH3:22])[CH2:4][CH2:3][CH2:2]1>C(O)C.[OH-].[OH-].[Pd+2]>[N:1]1([C:5](=[O:23])[CH2:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=2[O:21][CH3:22])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 895840151-(Azetidin-1-yl)-2-[4-(benzyloxy)-2-methoxyphenyl]ethanone

Product 1

HCID 895816361-(Azetidin-1-yl)-2-(4-hydroxy-2-methoxyphenyl)ethanone

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

1-(azetidin-1-yl)-2-[4-(benzyloxy)-2-methoxyphenyl]ethanone (1.26 g, 4.05 mmol) was dissolved in ethanol (10 ml) and palladium hydroxide on carbon (20%) (284 mg, 0.405 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 0-30% water: acetonitrile+0.05% formic acid to afford the title compound. LC/MS (m/z): 222 (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-d35f89709cd94a7abd407db7b7da5d43
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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