(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 264456노트

반응식

HRID 264456 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 82844Platinum oxide (PtO)촉매HCID 702Ethanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-ef92a5c58f3b480c99caaecf0b933365
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646173

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