Sodium Hydroxide → Ammonia

HRID 1266976Notes

Reaction equation

HRID 1266976 reaction equation
C[N:2]1[CH:8]2[CH2:9][CH2:10][CH:3]1[CH2:4][N:5]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:7]2.CCOC(/N=N/C(OCC)=O)=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[NH3:2].[C:14]([O:13][C:11]([N:5]1[CH2:6][CH2:7][CH:8]2[NH:2][CH:3]([CH2:10][CH2:9]2)[CH2:4]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5462977Diethyl azodicarboxylateHCID 18545171Tert-butyl 9-methyl-3,9-diazabicyclo[4.2.1]nonane-3-carboxylate

Product 2

HCID 222AmmoniaHCID 18545173tert-Butyl 3,9-diazabicyclo(4.2.1)nonane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9-Methyl-3-tert-butoxycarbonyl-3,9-diazabicyclo-[4.2.1]-nonane (3.4 g, 14.1 mmol), Diethylazodicarboxylate (12.3 g, 70.7 mmol) and toluene (35 ml) was stirred at reflux for 1.5 h. Sodiumhydroxide (50 ml, 1 M) was added. The aqueous phase was extracted twice with ethyl acetate (50 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as an oil. Yield 1.13 g, 35%.

Workup

  1. temperatureat reflux for 1.5 h
  2. extractionThe aqueous phase was extracted twice with ethyl acetate (50 ml)

Sources & evidence

ORD record
ord-21461191bc334ca5936a130bd7cecbda
Source dataset
uspto-grants-2003_04
Patent number
US06552012B2

Reaction notes

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