Ethanol → 2-Methyl-2,3,3a,8-tetrahydro-dibenzo [1,2:5,6]cyclohepta[3,4-c]pyrrole
Reaction equation
[CH3:1][N:2]1[CH2:6][C@@H:5]2[C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C@@H:4]2[C:3]1=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.C(O)C>CCOCC.O1CCCC1.CCOCC>[CH3:1][N:2]1[CH2:6][CH:5]2[C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:4]2=[CH:3]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
0.7 g cis-2-methyl-3,3a,8,12b-tetrahydro-dibenzo[1,2;5,6]cyclohepta[3,4-c]pyrrol-1(2H)-one is dissolved in 25 ml dry ether/tetrahydrofuran (1:1). This solution is slowly added at 0° C. to a suspension of 0.35 g LiAlH4 in 20 ml ether/t.h.f. (1:1). After stirring for 15 minutes, water is added and the mixture is then filtered. The filtrate is subsequently evaporaed to dryness under vacuum. This gives an oily residue, weighing about 0.7 g. Addition of 8 ml ethanol to this residue results in the formation of a precipitate, which is filtered off. [The crystalline product thus obtaned is recrystallized, giving 0.25 g 2-methyl-2,3,3a,8-tetrahydro-dibenzo [1,2:5,6]cyclohepta[3,4-c]pyrrole of melting point 128°-131° C. (=enamine according to formula III)].
Workup
- filtrationthe mixture is then filtered
- customThis gives an oily residue
- customresults in the formation of a precipitate, which
- filtrationis filtered off
- custom[The crystalline product thus obtaned is recrystallized
Sources & evidence
- ORD record
- ord-b80adba3e72c4ea08b133a10692144fc
- Source dataset
- uspto-grants-1981_06
- Patent number
- US04271178
Reaction notes
Loading…