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Bromochloromethane → (4S)-N-tert-butoxycarbonyl-5-chloromethyl-5-hydroxy-4-phenylmethyloxazolidine

HRID 413986
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 413986
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](=[O:20])[O:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][Cl:23].C([Li])CCC.S([O-])(O)(=O)=O.[K+]>CCCCCC.O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:11]([CH2:22][Cl:23])([OH:20])[O:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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Komponenten

7

Edukt 4

HCID 6333BromochloromethaneHCID 516920Potassium bisulfateHCID 11482799(4S)-N-Boc-4-phenylmethyloxazolidin-5-oneHCID 178418339Butyllithium

Produkt 1

HCID 15549468(4S)-N-tert-butoxycarbonyl-5-chloromethyl-5-hydroxy-4-phenylmethyloxazolidineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel
HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

(4S)-N-tert-butoxycarbonyl-4-phenylmethyloxazolidin-5-one (0.34 g) and bromochloromethane (0.10 ml) were added to dehydrated tetrahydrofuran (12 ml). After cooling to −78° C., 1.53 M solution (1.03 ml) of n-butyllithium in hexane was added to the obtained mixture, and they were stirred for 1 hour. 10% aqueous potassium hydrogensulfate solution was added to the reaction mixture to terminate the reaction. The temperature of the reaction mixture was elevated to room temperature. After the extraction with ethyl acetate twice, the obtained ethyl acetate layer was dried over anhydrous magnesium sulfate and then magnesium sulfate was removed. The solvent was evaporated under reduced pressure to obtain intended (4S)-N-tert-butoxycarbonyl-5-chloromethyl-5-hydroxy-4-phenylmethyloxazolidine (0.40 g) in a yield of 100%.

Aufarbeitung

  1. customto terminate
  2. customthe reaction
  3. customwas elevated to room temperature
  4. extractionAfter the extraction with ethyl acetate twice
  5. dry with materialthe obtained ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. custommagnesium sulfate was removed
  7. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-04f3ea0f039d4dcf92d1926a4d4273c0
Quelldatensatz
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06570039B2

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