2-[2-(Azetidin-1-yl)-2-oxoethyl]-5-(benzyloxy)benzonitrile → 2-[2-(Azetidin-1-yl)-2-oxoethyl]-5-hydroxybenzonitrile

HRID 1850729Notes

Reaction equation

HRID 1850729 reaction equation
[N:1]1([C:5](=[O:23])[CH2:6][C:7]2[CH:14]=[CH:13][C:12]([O:15]CC3C=CC=CC=3)=[CH:11][C:8]=2[C:9]#[N:10])[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:14]=[CH:13][C:12]([OH:15])=[CH:11][C:8]=2[C:9]#[N:10])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 708186342-[2-(Azetidin-1-yl)-2-oxoethyl]-5-(benzyloxy)benzonitrile

Product 1

HCID 708186242-[2-(Azetidin-1-yl)-2-oxoethyl]-5-hydroxybenzonitrile

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

2-[2-(azetidin-1-yl)-2-oxoethyl]-5-(benzyloxy)benzonitrile (410 mg, 1.34 mmol) was dissolved in ethanol (2 ml) and palladium hydroxide on carbon (20%) (94 mg, 0.134 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 0-25% water:acetonitrile+0.05% formic acid to afford the title compound. LC/MS (m/z): 217 (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-744ba09762ec426fbcb8bd0e36c4bd50
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

Loading…