Lysergic Acid → ((8beta)-9,10-Didehydro-6-methylergolin-8-yl)(1-pyrrolidinyl)methanone

HRID 1445717

反応式

HRID 1445717 の反応式
[OH:1][C:2]([C@@H:4]1[CH:19]=[C:18]2[C@@H:8]([CH2:9][C:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=4)[NH:12][CH:11]=3)[N:6]([CH3:7])[CH2:5]1)=O.[CH2:21]([N:23](CC)[CH2:24][CH3:25])[CH3:22].N1CCCC1>ClCCl>[CH3:7][N:6]1[C@H:8]2[C:18]([C:17]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:20]=3[C:10](=[CH:11][NH:12]4)[CH2:9]2)=[CH:19][C@@H:4]([C:2]([N:23]2[CH2:24][CH2:25][CH2:22][CH2:21]2)=[O:1])[CH2:5]1

参加物

5

反応物 3

HCID 6717Lysergic AcidHCID 8471TriethylamineHCID 31268Pyrrolidine

生成物 1

HCID 200628((8beta)-9,10-Didehydro-6-methylergolin-8-yl)(1-pyrrolidinyl)methanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

30 g (111.80 mmol) lysergic acid is dissolved in 400 ml dichloromethane and cooled to 0°-5° C., 31.16 ml (223.61, 2 eq.) triethylamine and 18.66 ml (223.61 mmol, 2 eq.) pyrrolidine is added and within 15 minutes 1.5 equivalents propanephosphonic acid anhydride (50% in ethyl acetate). The reaction mixture is stirred for 1 hour at room temperature, then it is poured onto ice and extracted with dichloromethane, the organic layer is dried with Na2SO4, evaporated and the residue (28.6 g) is purified by chromatography on silica eluting with dichloromethane:methanol 9:1 to give ((6aR,9R)-7-Methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinolin-9-yl)-pyrrolidin-1-yl-methanone.

後処理

  1. temperaturecooled to 0°-5° C.
  2. additionit is poured onto ice
  3. extractionextracted with dichloromethane
  4. dry with materialthe organic layer is dried with Na2SO4
  5. customevaporated
  6. customthe residue (28.6 g) is purified by chromatography on silica eluting with dichloromethane:methanol 9:1

出典と根拠

ORDレコード
ord-75eaf35c767f412ba9bcd460cd64a035
出典データセット
uspto-grants-2010_02
特許番号
US07666877B2

関連ノート

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