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Sodium Iodide → tert-Butyl 9-(pyridin-4-yloxy)-3-azaspiro[5.5]undecane-3-carboxylate

HRID 453911
Notes
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Reaction equation

HRID 453911 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[H-].[Na+].[OH:11][CH:12]1[CH2:29][CH2:28][C:15]2([CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH2:14][CH2:13]1.[I-].[Na+].C([O-])(O)=O.[Na+]>CS(C)=O.CO>[N:6]1[CH:7]=[CH:8][C:3]([O:11][CH:12]2[CH2:13][CH2:14][C:15]3([CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:17][CH2:16]3)[CH2:28][CH2:29]2)=[CH:4][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 818524-Chloropyridine hydrochlorideHCID 516892Sodium BicarbonateHCID 66701044tert-Butyl 9-hydroxy-3-azaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 66701182tert-Butyl 9-(pyridin-4-yloxy)-3-azaspiro[5.5]undecane-3-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 887MethanolSolvent

Procedure

4-Chloropyridine hydrochloride (1.3 g) was added to sodium hydride (0.89 g) in DMSO (20 ml), and the mixture was stirred for 10 min. tert-Butyl 9-hydroxy-3-azaspiro[5.5]undecane-3-carboxylate (2.0 g) in DMSO (20 ml) was then added slowly, and the mixture was stirred overnight (TLC monitoring: conversion about 30-35%). A catalytic amount of sodium iodide was added, and the reaction mixture was stirred for 8 h at 80° C. (TLC monitoring). Methanol and NaHCO3 solution were added to the reaction mixture, and stirring was carried out for 20 min. Extraction with ethyl acetate was then carried out, followed by washing with NaHCO3 solution and cold water. The organic phase was dried (Na2SO4) and concentrated under vacuum. The resulting crude product was purified by column chromatography (silica gel, 70% ethyl acetate/hexane). Yield: 1.0 g (40%)

Workup

  1. additionwas then added slowly
  2. stirringthe reaction mixture was stirred for 8 h at 80° C. (TLC monitoring)
  3. stirringstirring
  4. waitwas carried out for 20 min
  5. extractionExtraction with ethyl acetate
  6. washby washing with NaHCO3 solution and cold water
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. concentrationconcentrated under vacuum
  9. customThe resulting crude product was purified by column chromatography (silica gel, 70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4759e88456ef49ada152abe2d0d62db1
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492559B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes