N-(1-Adamantylmethyl)-5-chloro-2-(3-hydroxy-1-propynyl)isonicotinamide → N-(1-Adamantylmethyl)-5-chloro-2-(3-hydroxypropyl)isonicotinamide

HRID 1247580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247580
[C:1]12([CH2:11][NH:12][C:13](=[O:25])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([C:21]#[C:22][CH2:23][OH:24])[CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H][H]>[Rh]>[C:1]12([CH2:11][NH:12][C:13](=[O:25])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([CH2:21][CH2:22][CH2:23][OH:24])[CH:15]=3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Komponenten

4

Edukt 2

HCID 21906723N-(1-Adamantylmethyl)-5-chloro-2-(3-hydroxy-1-propynyl)isonicotinamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 21906688N-(1-Adamantylmethyl)-5-chloro-2-(3-hydroxypropyl)isonicotinamideAusbeute 62,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23948RhodiumKatalysator

Versuchsvorschrift

A stirred suspension of N-(1-adamantylmethyl)-5-chloro-2-(3-hydroxy-1-propynyl)isonicotinamide (Example 1 (iii)) (0.48 g) and 5% rhodium on carbon (0.020 g) was stirred under a positive pressure (3 barr) of hydrogen until no further uptake was observed. The mixture was filtered and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate to afford the sub-titled compound (0.305 g) as an oil.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e93cd577b26c4193acaf476d91274bf6
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129246B2

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