Water → tert-Butyl 4-((5-bromopyridin-2-yl)oxy)piperidine-1-carboxylate

HRID 2422672Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].[Br:17][C:18]1C=CN=[C:20](F)[CH:19]=1.O.[CH3:26][N:27]([CH:29]=O)C>C(OCC)(=O)C>[Br:17][C:18]1[CH:19]=[CH:20][C:26]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)=[N:27][CH:29]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Tert-butyl 4-hydroxytetrahydro-1(2H)-pyridinecarboxylate (10.0 g, 50.0 mmol) was dissolved in DMF (150 mL), and with stirring at 0° C., sodium hydride (purity 60%, 1.43 g) was added thereto. After stirred for 10 minutes, 4-bromo-2-fluoropyridine (8.75 g, 50.0 mmol) was added thereto and further stirred at room temperature for 20 hours. Water was added to the reaction solution and stirred for 10 minutes, and then the reaction solution was diluted with ethyl acetate, washed with water and saturated saline water in that order, and the organic layer was dried with magnesium sulfate. The solvent was evaporated off, and the residue was recrystallized from ethanol-water to obtain the intended compound (11 g) as a colorless solid.

Workup

stirringAfter stirred for 10 minutes
stirringfurther stirred at room temperature for 20 hours
stirringstirred for 10 minutes
washwashed with water and saturated saline water in that order
dry with materialthe organic layer was dried with magnesium sulfate
customThe solvent was evaporated off
customthe residue was recrystallized from ethanol-water

Sources & evidence

ORD record: ord-d21952618a074307b7a5bd6c8934dbe9
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960394B2

Reaction notes

Loading…