Thiophenol → (3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide

HRID 627169Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627169
[CH2:1]([O:4][N:5]([C@@H:18]1[C:23]([C:24]([N:26]([CH3:28])[CH3:27])=[O:25])=[CH:22][C@@H:21]([CH2:29][O:30][CH3:31])[NH:20][CH2:19]1)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1>C(#N)C>[CH2:1]([O:4][NH:5][C@@H:18]1[C:23]([C:24]([N:26]([CH3:28])[CH3:27])=[O:25])=[CH:22][C@@H:21]([CH2:29][O:30][CH3:31])[NH:20][CH2:19]1)[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 89851925(3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide2×

Produkt 1

HCID 89852322(3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamideAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of (3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide (Intermediate 141, 1.346 g, 2.96 mmol) and potassium carbonate (2.456 g, 17.77 mmol) in acetonitrile (50 mL) was added benzenethiol (1.825 mL, 17.77 mmol) and stirred at rt overnight. The solvent was evaporated then the crude mixture was redissolved in DCM and a little bit MeOH, filtered, loaded onto silica gel. The crude product was purified via flash chromatography (0-20% MeOH/DCM) and dried under high-vacuum to obtain the desired product (0.725 g, 91%) as a pale yellow oil.

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe crude mixture was redissolved in DCM
  3. filtrationa little bit MeOH, filtered
  4. customThe crude product was purified via flash chromatography (0-20% MeOH/DCM)
  5. customdried under high-vacuum

Quellen und Nachweise

ORD-Eintrag
ord-089c902999b34e3c89b581ca21f6656f
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309245B2

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