Reaktion #155585

ord-9bdc6922540b4cfbbeaf76020823ffdc

Reaktionsgleichung

C[C@H]1C[C@H]2CON[C@@]2(c2cccc(C#N)c2)CO1
3-[(3aR,5S,7aS)-5-Methyltetrahydro-1H-pyrano[3,4-c][1,2]oxazol-7a(7H)-yl]benzonitrile
C[C@H]1C[C@@H](CO)[C@](N)(c2cc(C#N)ccc2Cl)CO1
3-[(3S,4R,6S)-3-amino-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]-4-chlorobenzonitrile
→
C[C@H]1C[C@@H](CO)[C@](N)(c2cccc(C#N)c2)CO1
3-[(3S,4R,6S)-3-amino-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]benzonitrile

Edukte

C[C@H]1C[C@H]2CON[C@@]2(c2cccc(C#N)c2)CO1
3-[(3aR,5S,7aS)-5-Methyltetrahydro-1H-pyrano[3,4-c][1,2]oxazol-7a(7H)-yl]benzonitrile
C[C@H]1C[C@@H](CO)[C@](N)(c2cc(C#N)ccc2Cl)CO1
3-[(3S,4R,6S)-3-amino-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]-4-chlorobenzonitrile

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe resulting product was used in the next step without further purification

Vorschrift

3-[(3aR,5S,7aS)-5-Methyltetrahydro-1H-pyrano[3,4-c][1,2]oxazol-7a(7H)-yl]benzonitrile (C21) was converted to the product using the method described for the synthesis of 3-[(3S,4R,6S)-3-amino-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]-4-chlorobenzonitrile (C18) in Example 6. The resulting product was used in the next step without further purification. Yield: 105 mg, 0.426 mmol, 60%. LCMS m/z 247.1 [M+H+].

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08822456B2uspto-grants-2014_09