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4-Fluorophenol → (7S,8aS)-7-(4-Fluorophenoxy)methyl-2-(5-cyanophenyl)-1,2,3,4,6,7,8,8 a-octahydro-pyrrolo[1,2-a]pyrazine

HRID 861349
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 861349
[OH:1][CH2:2][C@@H:3]1[CH2:19][N:6]2[CH2:7][CH2:8][N:9]([C:11]3[CH:16]=[CH:15][C:14](C#N)=[CH:13][CH:12]=3)[CH2:10][C@@H:5]2[CH2:4]1.[F:20][C:21]1[CH:26]=[CH:25][C:24](O)=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:47]([C:54](OCC)=O)=NC(OCC)=O>C1COCC1>[F:20][C:21]1[CH:26]=[CH:25][C:24]([O:1][CH2:2][C@@H:3]2[CH2:19][N:6]3[CH2:7][CH2:8][N:9]([C:11]4[CH:12]=[C:13]([C:54]#[N:47])[CH:14]=[CH:15][CH:16]=4)[CH2:10][C@@H:5]3[CH2:4]2)=[CH:23][CH:22]=1
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Komponenten

6

Edukt 4

HCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 57229001(7S,8aS)-7-hydroxymethyl-2-(4-cyanophenyl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

Produkt 1

HCID 67648213(7S,8aS)-7-(4-Fluorophenoxy)methyl-2-(5-cyanophenyl)-1,2,3,4,6,7,8,8 a-octahydro-pyrrolo[1,2-a]pyrazine
Ausbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 0.25 g (0.97 mmol) of (7S,8aS)-7-hydroxymethyl-2-(4-cyanophenyl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Preparation 16), 0.164 g (1.46 mmol) of 4-fluorophenol, 0.31 g (1.15 mmol) of triphenylphosphine in 10 mL of THF was treated with 0.18 mL (1.15 mmol) of diethyl azodicarboxylate and the solution stirred at ambient temperature for 16 h. The solvent was removed by rotary evaporation, and the residue partitioned between chloroform and 1M sodium hydroxide. The layers were separated, and the organic phase was dried (magnesium sulfate), filtered and evaporated. Purification by flash silica gel chromatography with 1:1 ethyl acetate:hexane gave 0.225 g (66%) of the title compound. mp (.HCl) 81°-85° C. HRMS calcd for C21H23FN3O (MH+): 352.1825, found: 352.1817.

Aufarbeitung

  1. customThe solvent was removed by rotary evaporation
  2. customthe residue partitioned between chloroform and 1M sodium hydroxide
  3. customThe layers were separated
  4. dry with materialthe organic phase was dried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash silica gel chromatography with 1:1 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-fa9c9f61f32044c98a357e147565c601
Quelldatensatz
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05714487

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