Acetonitrile → 1,5-Diazabicyclo(4.3.0)non-5-ene

HRID 1870875Notes

Reaction equation

HRID 1870875 reaction equation
[N+:1]([CH3:4])([O-])=O.[N+:5]([CH2:8][CH3:9])([O-])=O.[C:10](#[N:12])[CH3:11].[CH2:13]1[CH2:17]O[CH2:15][CH2:14]1>C(N(CC)CC)C>[CH2:11]1[CH2:10][N:12]2[C:8](=[N:5][CH2:14][CH2:13][CH2:17]2)[CH2:9]1.[CH2:14]1[CH2:13][CH2:17][N:1]2[C:8](=[N:5][CH2:10][CH2:11][CH2:4]2)[CH2:9][CH2:15]1

Participants

7

Reactant 4

HCID 6342Acetonitrile2×HCID 6375NitromethaneHCID 6587NitroethaneHCID 8028Tetrahydrofuran

Product 2

HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In Step 2, ester 24 is reacted with a substituted or unsubstituted nitroalkane, such as nitromethane or nitroethane, in a polar aprotic solvent, such as acetonitrile, THF or the like, preferably acetonitrile, in the presence of an amine base, such as DBU, DBN, triethylamine or the like, preferably DBU, at a temperature from 0° to 80° C., preferably 25° C., for 24 h to yield nitro ester 25. ##STR29##

Sources & evidence

ORD record
ord-4ee7b72a8e064a389b503bcda804e972
Source dataset
uspto-grants-2000_08
Patent number
US06100279

Reaction notes

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