(R)-3-(5-bromo-pyridin-3-yloxy)-piperidine-1-carboxylic acid tert-butyl ester → 3-bromo-5-((R)-piperidin-3-yloxy)-pyridine

HRID 712720Notes

Reaction equation

HRID 712720 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([O:14][C:15]2[CH:16]=[N:17][CH:18]=[C:19]([Br:21])[CH:20]=2)[CH2:9]1)=O)(C)(C)C>CO.Cl.O1CCOCC1>[Br:21][C:19]1[CH:18]=[N:17][CH:16]=[C:15]([O:14][C@@H:10]2[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH:20]=1

Participants

5

Reactant 1

HCID 117667237(R)-3-(5-bromo-pyridin-3-yloxy)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 1176675653-bromo-5-((R)-piperidin-3-yloxy)-pyridineYield 120.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (R)-3-(5-bromo-pyridin-3-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (596 mg, 1.7 mmol) in MeOH (5 mL) and HCl solution in 1,4-dioxane (4N; 1.5 mL) is stirred at room temperature for 16 h. The mixture is concentrated to provide 525 mg 3-bromo-5-((R)-piperidin-3-yloxy)-pyridine as the hydrochloride salt.

Workup

  1. concentrationThe mixture is concentrated

Sources & evidence

ORD record
ord-8237b17ba3c44a49b679c8846484354f
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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