(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-ethyl-5-oxo-5,6-dihydropyridine-1 (2H)-carboxylate → (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-ethyl-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627220Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627220
[Si:1]([O:8][CH2:9][C@@H:10]1[C:15]([CH2:16][CH3:17])=[CH:14][C:13](=[O:18])[CH2:12][N:11]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si](OC[C@@H]1C=C(C)[C@H](O)CN1C(OC(C)(C)C)=O)(C(C)(C)C)(C)C>>[Si:1]([O:8][CH2:9][C@@H:10]1[C:15]([CH2:16][CH3:17])=[CH:14][C@H:13]([OH:18])[CH2:12][N:11]1[C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Komponenten

3

Edukt 2

HCID 89852241(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-ethyl-5-oxo-5,6-dihydropyridine-1 (2H)-carboxylate2×HCID 89852486tert-Butyl (3S,6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-3-hydroxy-4-methyl-1,2,3,6-tetrahydropyridine-1-carboxylate

Produkt 1

HCID 89852682(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-ethyl-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylateAusbeute 100,3 %

Versuchsvorschrift

The title compound was prepared from (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-ethyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 207, 5.146 g, 13.92 mmol) according to the procedure described for Intermediate 8, except the mixture was stirred at ambient temperature for 1 h. The mixture was concentrated and diluted with aqueous NH4Cl, water and EtOAc. The organic layer was separated and washed three times with brine, dried over Na2SO4, filtered and concentrated to afford the title compound (5.19 g, 100%) as a cloudy oil.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. additiondiluted with aqueous NH4Cl, water and EtOAc
  3. customThe organic layer was separated
  4. washwashed three times with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-51f0c8a30e7a4d1a985770e501bd5612
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309245B2

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