Sodium Hydroxide → Ammonia

HRID 1266975Notes

Reaction equation

HRID 1266975 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH:13]2[NH:16][CH:10]([CH2:11][CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:18]1[CH:19]=[N:20][CH:21]=[C:22]([O:24][CH2:25][CH3:26])[CH:23]=1.CC(C)([O-])C.[K+].[OH-].[Na+]>COCCOC>[NH3:8].[CH2:25]([O:24][C:22]1[CH:23]=[C:18]([N:16]2[CH:13]3[CH2:12][CH2:11][CH:10]2[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:15][CH2:14]3)[CH:19]=[N:20][CH:21]=1)[CH3:26]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 115211283-Chloro-5-ethoxypyridineHCID 18545173tert-Butyl 3,9-diazabicyclo(4.2.1)nonane-3-carboxylateHCID 23665647Potassium tert-butoxide

Product 2

HCID 222AmmoniaHCID 120512859-[5-Ethoxy-(3-pyridyl)]-3-tert-butoxycarbonyl-3,9-diazabicyclo-[4.2.1]-nonane

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3-tert-butoxycarbonyl-3,9-diazabicyclo-[4.2.1]-nonane (1.1 g, 4.9 mmol), 3-chloro-5-ethoxypyridine (0.77 g, 4.9 mmol), potassium-tert-butoxide (1.09 g, 9.7 mmol) and 1,2-dimethoxyethane (20 ml) was heated at reflux for 1.5 h. Sodium hydroxide (30 ml, 1 M) was added and the aqueous phase was extracted twice with ethyl acetate (30 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as an oil. Yield 0.24 g, 14%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. extractionthe aqueous phase was extracted twice with ethyl acetate (30 ml)

Sources & evidence

ORD record
ord-d223952b33a4401db3eadf2ed83cfcc1
Source dataset
uspto-grants-2003_04
Patent number
US06552012B2

Reaction notes

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