Pyridine → 1-((6,6-Dimethylbicyclo[3,1,1]hept-3-yl)methyl)-3-mehtyl-3-pyrroline-2,5-dione
Reaction equation
[C:1]1(=[O:8])O[C:5](=[O:6])[CH:4]=[C:2]1[CH3:3].[CH3:9][C:10]1([CH3:19])[C@H:15]2[CH2:16][C@@H:11]1[CH2:12][CH2:13][C@H:14]2CN.[N:20]1C=CC=C[CH:21]=1>>[CH3:19][C:10]1([CH3:9])[CH:11]2[CH2:16][CH:15]1[CH2:14][CH:13]([CH2:21][N:20]1[C:5](=[O:6])[CH:4]=[C:2]([CH3:3])[C:1]1=[O:8])[CH2:12]2Participants
4
Conditions
- Temperature
- 90 °C
Procedure
A solution of citraconic anhydride (0.1 M) in pyridine (20 ml)was treated with (−)-cis-myrtanylamine (0.1 M). The reaction mixture was heated to 90° C. for six hours. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product.
Workup
- concentrationThe reaction mixture was then concentrated in vacuo
- extractionthe residue was extracted into ethyl acetate
- washThe ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid
- dry with materialdried over sodium sulphate
- concentrationfinally concentrated in vacuo
- customThe residue obtained
- customwas chromatographed over silica gel
Sources & evidence
- ORD record
- ord-dba6e1788a3f43ae8559cb0269fa31f8
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06476053B1
Reaction notes
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