3-Amino-1-adamantanol → (2S,5R)-5-ethynyl-1-{N-((5R,7S)-3-hydroxy-1-adamantyl)glycyl}pyrrolidine-2-carbonitrile

HRID 855891

Reaktionsgleichung

Reaktionsgleichung von HRID 855891
Cl[CH2:2][C:3]([N:5]1[C@@H:9]([C:10]#[CH:11])[CH2:8][CH2:7][C@H:6]1[C:12]#[N:13])=[O:4].[NH2:14][C:15]12[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][C:17]([OH:25])([CH2:18]3)[CH2:16]1)[CH2:22]2>C(#N)C>[C:10]([C@@H:9]1[N:5]([C:3](=[O:4])[CH2:2][NH:14][C:15]23[CH2:24][C@H:19]4[CH2:20][C@H:21]([CH2:23][C:17]([OH:25])([CH2:18]4)[CH2:16]2)[CH2:22]3)[C@H:6]([C:12]#[N:13])[CH2:7][CH2:8]1)#[CH:11]

Komponenten

4

Edukt 2

HCID 6586453-Amino-1-adamantanolHCID 16090854(2S,5R)-1-(2-chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile

Produkt 1

HCID 9973731(2S,5R)-5-ethynyl-1-{N-((5R,7S)-3-hydroxy-1-adamantyl)glycyl}pyrrolidine-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of Example 8D (0.06 g, 0.305 mmol) in acetonitrile (3 mL) at room temperature under nitrogen, was added 3-amino-1-adamantanol (0.1 g, 0.61 mmol). The reaction mixture was stirred for two days and then concentrated under reduced pressure. The residue was flash chromatographed with 5-7% MeOH/CH2Cl2 to provide the desired compound as a pale yellow oil. MS (DCI) m/z 328 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 1.5-2 (14H, m), 2.11-2.21 (2H, m), 2.45-2.48 (2H, m), 3.78 (1H, d), 3.8-4.5 (2H, m), 4.53-4.55 (1H, t), 5.01 (1H, m), 5.05 (1H, m).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customchromatographed with 5-7% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-2aee87f7866c4b93b3047e59f57ca720
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262207B2

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