2,6-Dichloropyridine → Tert-butyl 4-[(6-chloropyridin-2-yl)oxy]piperidine-1-carboxylate

HRID 1467987

Reaction equation

HRID 1467987 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Cl)[N:19]=1>C1COCC1>[Cl:17][C:18]1[N:19]=[C:20]([O:14][CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 169892,6-DichloropyridineHCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 21906058Tert-butyl 4-[(6-chloropyridin-2-yl)oxy]piperidine-1-carboxylateYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4-Hydroxy-piperidine-1-carboxylic acid tert-butyl ester (1.63 g, 8.1 mmol) in THF (20 mL), NaH (0.40 g, 10.1 mmol)) was added and stirred at 60° C. for 0.5 h. 2,6-dichloropyridine (1.0 g, 6.75 mmol) was added and stirred at room temperature for 3-4-h. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was concentrated in vacuo and the resultant residue was purified by flash column chromatography to yield tert-butyl 4-((6-chloropyridin-2-yl)oxy)piperidine-1-carboxylate as a pale yellow solid (0.98 g, 48%); MS: 335.1 (M+23)

Workup

  1. stirringstirred at room temperature for 3-4-h
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe resultant residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-6b98d450d34d4947afe804c798f92a1c
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Linked notes

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