(R)-1-(2-azido-propyl)-4,5-dihydro-8-methoxy-1H-benz[g]indole → (R)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethylamine
Reaction equation
[N:1]([C@H:4]([CH3:21])[CH2:5][N:6]1[C:14]2[C:13]3[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:12]=3[CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7]1)=[N+]=[N-]>C(O)C.[Pt]=O>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:12]2[CH2:11][CH2:10][C:9]3[CH:8]=[CH:7][N:6]([CH2:5][C@H:4]([NH2:1])[CH3:21])[C:14]=3[C:13]=2[CH:15]=1Participants
Procedure
1.9 g of (R)-1-(2-azido-propyl)-4,5-dihydro-8-methoxy-1H-benz[g]indole dissolved in 100 ml of anhydrous ethanol were hydrogenated on 190 mg of platinum oxide for 16 hours. The catalyst was subsequently filtered off, rinsed with ethonal and the solvent was drawn off in a vacuum. There were obtained 1.64 g (95%) of (R)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethylamine as a colorless oil, of which 440 mg were dissolved in 70 ml of anhydrous ether, filtered and treated while stirring with a solution of 200 mg of fumaric acid in 20 ml of methanol the mixture was stirred at room temperature for 2 hours and the white crystals were subsequently filtered off. 450 mg (70%) of (R)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethylamine fumarate (1:1) with m.p. 194° were obtained.
Workup
- filtrationThe catalyst was subsequently filtered off
- washrinsed with ethonal and the solvent
Sources & evidence
- ORD record
- ord-ef92a5c58f3b480c99caaecf0b933365
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05646173
Reaction notes
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