tert-butyl (2R,5S)-2-[(2-aminopyridin-3-yl)ethynyl]-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)morpholine-4-carboxylate → tert-butyl (2R,5S)-2-[2-(2-aminopyridin-3-yl)ethyl]-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)morpholine-4-carboxylate

HRID 629706

Reaktionsgleichung

Reaktionsgleichung von HRID 629706
[NH2:1][C:2]1[C:7]([C:8]#[C:9][C@H:10]2[O:15][CH2:14][C@@H:13]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[N:12]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:11]2)=[CH:6][CH:5]=[CH:4][N:3]=1>FC(F)(F)CO.[Pd]>[NH2:1][C:2]1[C:7]([CH2:8][CH2:9][C@H:10]2[O:15][CH2:14][C@@H:13]([CH2:16][O:17][Si:18]([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:19])[CH3:20])[N:12]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:11]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

4

Edukt 1

HCID 86726311tert-butyl (2R,5S)-2-[(2-aminopyridin-3-yl)ethynyl]-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)morpholine-4-carboxylate

Produkt 1

HCID 86726313tert-butyl (2R,5S)-2-[2-(2-aminopyridin-3-yl)ethyl]-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)morpholine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 64092,2,2-TrifluoroethanolLösungsmittel

Versuchsvorschrift

To tert-butyl (2R,5S)-2-[(2-aminopyridin-3-yl)ethynyl]-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)morpholine-4-carboxylate (1 eq.) in 2,2,2,-trifluoroethanol (0.4 M) at rt was added 10% Pd/C (0.2 eq.). The reaction was degassed and then shaken under 1 atm of H2 for 24 hrs. The reaction mixture was filtered on celite and concentrated to afford the desired compound.

Aufarbeitung

  1. customThe reaction was degassed
  2. filtrationThe reaction mixture was filtered on celite
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-89f2c3218b814a1681e58a1876a17109
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315475B2

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