Ammonia → HCID 86596732, compound
Reaction equation
CI.[C:3]123[CH2:16][CH2:15][CH2:14][C:8]1([C:9](=O)[NH:10][C:11]2=O)[CH:7]1[CH2:17][CH:4]3[CH:5]=[CH:6]1.N.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[C:8]123[CH2:14][CH2:15][CH2:16][C:3]1([CH2:11][NH:10][CH2:9]2)[CH:4]1[CH2:17][CH:7]3[CH:6]=[CH:5]1Participants
Procedure
Template A is synthesized by quaternization of 8-aza-8-ethyltetracyclo[4.3.3.12,5.01,6]tridec-3-ene with methyl iodide. Templates C-E are all made using the methodology described above. The parent imide, 8-aza-tetracyclo[4.3.3.12,5.01,6]tridec-3-ene-7,9-dione, is synthesized by reacting the tetracyclic anhydride with ammonia, which upon LiAlH4-reduction yields the unsubstituted secondary cyclic amine, 8-aza-tetracyclo[4.3.3.12,5.01,6]tridec-3-ene. Quaternization of this amine with the appropriate dihalide in the presence of KHCO3 yields the desired template (Template C from 1,4-diiodobutane, Template D from 1,5-diiodobutane, and Template E from 2-methyl-1,4-diiodobutane). It is to be anticipated that other derivatives can be prepared by the choice of the imide forming reagent coupled with choices for the alkylation step.
Sources & evidence
- ORD record
- ord-1277719a1450474fa6e1fe1b44c48c61
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06929789B2
Reaction notes
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