Ethylene Glycol → HCID 178517853, Verbindung

HRID 2205646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2205646
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][C@:10]3([CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)[C:9]2=[O:18])[CH2:4][CH2:3]1.[Br:19][C:20]1[CH:25]=[CH:24][C:23](I)=[C:22]([F:27])[CH:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>C(O)CCC.[Cu]I>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([N:14]2[CH2:15][CH2:16][CH2:17][C@@:10]3([C:9](=[O:18])[N:8]([C@H:5]4[CH2:6][CH2:7][C@@H:2]([OH:1])[CH2:3][CH2:4]4)[CH2:12][CH2:11]3)[CH2:13]2)=[C:22]([F:27])[CH:21]=1

Komponenten

7

Edukt 4

HCID 174Ethylene GlycolHCID 62657Potassium Phosphate, TribasicHCID 27245164-Bromo-2-fluoro-1-iodobenzeneHCID 178517863HCID 178517863, Verbindung

Produkt 1

HCID 178517853HCID 178517853, VerbindungAusbeute 54,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of (5S)-2-(cis-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one (1.04 g, 0.00412 mol), 4-bromo-2-fluoro-1-iodobenzene (Aldrich, cat #: 283304) (1.85 g, 0.00615 mol), copper(I) iodide (Aldrich, cat #: 215554) (0.122 g, 0.000640 mol), potassium phosphate (2.63 g, 0.0124 mol) and 1,2-ethanediol (0.48 mL, 0.0086 mol) in 1-butanol (3.90 mL) was heated at 100° C. under nitrogen for 2 d. The reaction was quenched with water, and extracted with ether. The organic layers were combined, washed with water, brine, dried over Na2SO4, and filtered. The filtrate was evaporated under reduced pressure. The residue was purified by flash column chromatography on a silica gel column eluting with 0 to 5% methanol in DCM to yield the desired product (950 mg, 54.2%). LC/MS m/e 425.1/427.0 (M+H)+.

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionextracted with ether
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customThe residue was purified by flash column chromatography on a silica gel column
  8. washeluting with 0 to 5% methanol in DCM

Quellen und Nachweise

ORD-Eintrag
ord-29fac59f7124407bbdb6383b02d7babb
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09371323B2

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