2-(Azetidin-3-yloxy)-3-(3,6-dihydro-2H-pyran-4-YL)pyridine hydrochloride → 2-(azetidin-3-yloxy)-3-(tetrahydro-2H-pyran-4-yl)pyridine

HRID 454908Notes

Reaction equation

HRID 454908 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([O:6][C:7]2[C:12]([C:13]3[CH2:14][CH2:15][O:16][CH2:17][CH:18]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:3]1>CO.[Pd]>[NH:2]1[CH2:3][CH:4]([O:6][C:7]2[C:12]([CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:5]1

Participants

4

Reactant 1

HCID 674774502-(Azetidin-3-yloxy)-3-(3,6-dihydro-2H-pyran-4-YL)pyridine hydrochloride

Product 1

HCID 585477652-(azetidin-3-yloxy)-3-(tetrahydro-2H-pyran-4-yl)pyridineYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 2-(azetidin-3-yloxy)-3-(3,6-dihydro-2H-pyran-4-yl)pyridine hydrochloride (see PREPARATION P26.1; 3.5 g, 15 mmol) and wet Pd—C (50%, 1.0 g) in MeOH (100 ml) was stirred under H2 (40 psi) at 30° C. for 3 hours then the reaction mixture was filtered through CELITE® and the filtrate was concentrated in vacuo to give the title compound (3.2 g, 14.6 mmol, yield 91%).

Workup

  1. filtrationthe reaction mixture was filtered through CELITE®
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bf1e0e2146dd457d8b9c5e9e987f429a
Source dataset
uspto-grants-2013_07
Patent number
US08497265B2

Reaction notes

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