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Ethyl Acetate → 2-(trimethylsilyl)ethyl rac-[(1R,2S,3R)-2,3-dihydroxy-1-methyl-2,3-dihydro-1H-inden-1-yl]carbamate

HRID 64454
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 64454
[OH:1][C@H:2]1[C@@H:10]([OH:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1([NH:13][C:14](=[O:22])[O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH3:12].[H-].[Na+].[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1>[OH:1][C@@H:2]1[C@H:10]([OH:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@:3]1([NH:13][C:14](=[O:22])[O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH3:12].[OH:11][CH:10]1[CH:2]2[C:3]([CH3:12])([NH:13][C:14](=[O:15])[O:22]2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]1=2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 90072640HCID 90072640, Verbindung

Produkt 2

HCID 900724932-(trimethylsilyl)ethyl rac-[(1R,2S,3R)-2,3-dihydroxy-1-methyl-2,3-dihydro-1H-inden-1-yl]carbamate
HCID 90073026
rac-(3aR,8S,8aR)-8-hydroxy-3a-methyl-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 130 mg of 2-(trimethylsilyl)ethyl rac-[(2R,3S)-2,3-dihydroxy-1-methyl-2,3-dihydro-1H-inden-1-yl]carbamate in 4 ml of THF was added 70 mg of 55% sodium hydride under ice-cooling, followed by stirring at the same temperature for 1 hour. To the reaction mixture were added a saturated aqueous ammonium chloride solution and ethyl acetate to carry out a layer separation operation, followed by drying over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 70 mg of 2-(trimethylsilyl)ethyl rac-[(1R,2S,3R)-2,3-dihydroxy-1-methyl-2,3-dihydro-1H-inden-1-yl]carbamate and 45 mg of rac-(3aR,8S,8aR)-8-hydroxy-3a-methyl-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazol-2-one.

Aufarbeitung

  1. temperaturecooling
  2. customa layer separation operation
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3121d4e780d9404b9e78699b502a3777
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09447090B2

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