Ethanol → (R)-tert-butyl 4-((1R,2S)-1-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 1499469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1499469
[Li+].[BH4-].C([C@@H]1COC(=O)N1[C:16](=[O:42])[C@H:17]([CH3:41])[C@H:18]([C@H:27]1[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[N:28]1[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])C1C=CC=CC=1.CCO>C1COCC1.CCOCC.[OH-].[Na+]>[Si:20]([O:19][C@@H:18]([C@H:27]1[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[N:28]1[C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[C@@H:17]([CH3:41])[CH2:16][OH:42])([C:23]([CH3:24])([CH3:25])[CH3:26])([CH3:22])[CH3:21]

Komponenten

7

Edukt 3

HCID 702EthanolHCID 4148881Lithium borohydrideHCID 68547408(R)-tert-butyl 4-((1R,2R)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-(tert-butyldimethylsilyloxy)-2-methyl-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate

Produkt 1

HCID 59226545(R)-tert-butyl 4-((1R,2S)-1-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylateAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

LiBH4 (0.25 g, 11 mmol) was added to a mixture of tert-butyl (4R)-4-((1R,2R)-3-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-1-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-3-oxopropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (2.2 g, 3.8 mmol) and EtOH (0.67 mL, 11 mmol) in THF (40 mL) at −30° C. The mixture was allowed to warm to 0° C. and stirred for 3 h. The reaction mixture was then diluted with ether and 1N NaOH was added. The resulting mixture was extracted with EtOAc. The organic extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0-20% EtOAc in hexanes) to afford the sub-title compound (1.2 g, 78%). LCMS calc. for C15H34NO3Si (M+H-Boc)+: m/z=304.2. found 304.2.

Aufarbeitung

  1. additionwas added
  2. extractionThe resulting mixture was extracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (0-20% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-eee0cb86f94f444ca75c5aa23d2afc2d
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09200004B2

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