Ammonia → Ergoline-8-methanol, 2-bromo-9,10-didehydro-6-methyl-, (8beta)-

HRID 1723027ノート

反応式

HRID 1723027 の反応式
[BrH:1].[OH-].[Na+].[OH:4][CH2:5][C@@H:6]1[CH:21]=[C:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[NH:14][CH:13]=3)[N:8]([CH3:9])[CH2:7]1.N>Br.CS(C)=O.CS(C)=O>[Br:1][C:13]1[NH:14][C:15]2[C:22]3[C:12]=1[CH2:11][C@@H:10]1[C:20]([C:19]=3[CH:18]=[CH:17][CH:16]=2)=[CH:21][C@@H:6]([CH2:5][OH:4])[CH2:7][N:8]1[CH3:9]

参加物

7

反応物 4

HCID 222AmmoniaHCID 260Hydrogen Bromide4 回HCID 14798Sodium HydroxideHCID 14987Lysergol

生成物 1

HCID 181032Ergoline-8-methanol, 2-bromo-9,10-didehydro-6-methyl-, (8beta)-

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 86743321HCID 86743321、化合物溶媒

実験手順

Dry gaseous hydrogen bromide is introduced into 100 ml of anhydrous dimethylsulfoxide at room temperature. The quantity of the introduced hydrogen bromide gas is measured by titrating with 0.1N sodium hydroxide solution. The hydrogen bromide is introduced until the concentration of the gas reaches 0.0003-0.0005 mole/ml. One g (0.003937 mole) of lysergol is dissolved in an aliquot amount of this hydrogen bromide-dimethylsulfoxide mixture which contains 12 equivalents of hydrogen bromide. After complete dissolution, this mixture is stirred at room temperature for 20 minutes, then poured into a 5-fold volume of ice-water. Thereafter, the solution is made alkaline by adding aqueous ammonia up to a pH value of 8.9, the precipitate is filtered off, washed with water, dried and purified on a Kieselgel column by using an 8:2 mixture of chloroform and methanol to give the named compound in a yield of 0.76 g (0.00228 mole, 58%), m.p.: 193° C.

後処理

  1. dissolutionAfter complete dissolution
  2. filtrationthe precipitate is filtered off
  3. washwashed with water
  4. customdried
  5. custompurified on a Kieselgel column
  6. additionan 8:2 mixture of chloroform and methanol
  7. customto give the named compound in a yield of 0.76 g (0.00228 mole, 58%), m.p.: 193° C.

出典と根拠

ORDレコード
ord-7c40ca1910e946b4ba0b0e83acfaf28b
出典データセット
uspto-grants-1989_08
特許番号
US04859682

反応ノート

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