Ethanol → 2-Methyl-2,3,3a,8-tetrahydro-dibenzo [1,2:5,6]cyclohepta[3,4-c]pyrrole

HRID 236867Notes

Reaction equation

HRID 236867 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]1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 86736413cis-2-methyl-3,3a,8,12b-tetrahydro-dibenzo[1,2;5,6]cyclohepta[3,4-c]pyrrol-1(2H)-one

Product 1

HCID 705722482-Methyl-2,3,3a,8-tetrahydro-dibenzo [1,2:5,6]cyclohepta[3,4-c]pyrroleYield 38%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21868444Ether tetrahydrofuranSolvent

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 evaporated 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 obtained 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

  1. filtrationthe mixture is then filtered
  2. customThe filtrate is subsequently evaporated to dryness under vacuum
  3. customThis gives an oily residue
  4. customresults in the formation of a precipitate, which
  5. filtrationis filtered off
  6. custom[The crystalline product thus obtained
  7. customis recrystallized

Sources & evidence

ORD record
ord-fa170f90786349baaf6ff7b115308a4d
Source dataset
uspto-grants-1979_06
Patent number
US04158059

Reaction notes

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