(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

HRID 264456ノート

反応式

HRID 264456 の反応式
[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]=1

参加物

4

反応物 1

HCID 54279251(R)-1-(2-azido-propyl)-4,5-dihydro-8-methoxy-1H-benz[g]indole

生成物 1

HCID 22874712(R)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethylamine収率 95.1%

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  1. filtrationThe catalyst was subsequently filtered off
  2. washrinsed with ethonal and the solvent

出典と根拠

ORDレコード
ord-ef92a5c58f3b480c99caaecf0b933365
出典データセット
uspto-grants-1997_07
特許番号
US05646173

反応ノート

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