Ammonium Chloride → rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-propyl-1H-benzo[e]indole
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:21]2[CH2:20][CH2:19][C@H:18]3[C@H:14]([CH2:15][CH2:16][N:17]3[C:22](=O)[CH2:23][CH3:24])[C:13]=2[CH:12]=[CH:11][CH:10]=1.[NH4+].[Cl-]>C1COCC1>[CH3:7][O:8][C:9]1[C:21]2[CH2:20][CH2:19][C@H:18]3[C@H:14]([CH2:15][CH2:16][N:17]3[CH2:22][CH2:23][CH3:24])[C:13]=2[CH:12]=[CH:11][CH:10]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
0.90 g (0.0232 mol) of lithium aluminum hydride was suspended in 40 ml of THF under argon. A solution of 3.0 g (0.0116 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-propionyl-1H-benzo[e]indole in 50 ml of THF was added dropwise thereto and the mixture was boiled under reflux for 1 hour. 25 ml of a saturated aqueous NH4Cl solution was cautiously added dropwise thereto, the mixture was filtered and the filtrate was extracted with ethyl acetate. The organic phase was washed with water, dried with MgSO4, filtered and concentrated. By chromatography of the residue over silica gel with CH2Cl2 /MeOH 49:1 there were obtained 2.65 g (93%) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-propyl-1H-benzo[e]indole as a colorless, oily material.
Workup
- temperatureunder reflux for 1 hour
- filtrationthe mixture was filtered
- extractionthe filtrate was extracted with ethyl acetate
- washThe organic phase was washed with water
- dry with materialdried with MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c83643d80ce145528222a2aaddc033dd
- Source dataset
- uspto-grants-1994_06
- Patent number
- US05318967
Reaction notes
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