Acetic Anhydride → 8-Azabicyclo[4.3.0]non-2-ene

Reaction equation

[CH2:1]([NH:4][CH2:5]/[CH:6]=[CH:7]/[CH:8]=[CH2:9])[CH:2]=[CH2:3].C(OC(=O)C)(=O)C>>[CH:6]12[CH2:5][NH:4][CH2:1][CH:2]1[CH2:3][CH2:9][CH:8]=[CH:7]2

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 12288410(E)-1-(2-propenylamino)-2,4-pentadiene

Product 1

HCID 123867678-Azabicyclo[4.3.0]non-2-ene

Procedure

Introduce 24.6 g (0.2 mol) of (E)-1-(2-propenylamino)-2,4-pentadiene (title compound of Example A.2.), dropwise add 22.4 g of acetic anhydride, and stir overnight at room temperature. Concentrate and react further in the form of the crude product.

Sources & evidence

ORD record: ord-68229a23502649168ffa78018f4a430a
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05854241

Reaction notes

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