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

HRID 1445717

Reaktionsgleichung

Reaktionsgleichung von HRID 1445717
[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

Komponenten

5

Edukt 3

HCID 6717Lysergic AcidHCID 8471TriethylamineHCID 31268Pyrrolidine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-75eaf35c767f412ba9bcd460cd64a035
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666877B2

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