StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Lithiumtriethylborohydride → 3-[(S)-1-(4-Bromo-2-methyl-phenyl)-ethyl]-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one

HRID 2036544
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2036544
C([BH-](CC)CC)C.[Li+].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]([N:18]2[CH2:23][CH2:22][C@:21]([CH2:30][C:31]3([CH3:34])[CH2:33][O:32]3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:20][C:19]2=[O:35])[CH3:17])=[C:12]([CH3:36])[CH:11]=1>O1CCCC1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]([N:18]2[CH2:23][CH2:22][C@:21]([CH2:30][C:31]([OH:32])([CH3:34])[CH3:33])([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:20][C:19]2=[O:35])[CH3:17])=[C:12]([CH3:36])[CH:11]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 23664628LithiumtriethylborohydrideHCID 581023913-[(S)-1-(4-Bromo-2-methyl-phenyl)-ethyl]-(S)-6-(2-methyl-oxiranylmethyl)-6-phenyl-[1,3]oxazinan-2-one

Produkt 1

HCID 581023933-[(S)-1-(4-Bromo-2-methyl-phenyl)-ethyl]-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium triethylborohydride (1 mol/L in tetrahydrofuran, 4.2 mL) was added to an ice-cold solution of 3-[(S)-1-(4-bromo-2-methyl-phenyl)-ethyl]-(S)-6-(2-methyl-oxiranylmethyl)-6-phenyl-[1,3]oxazinan-2-one (1.55 g, ca. 85-90% pure) in tetrahydrofuran (15 mL) at such a rate that the solution temperature remained below 10° C. The resulting solution was stirred in the cooling bath for one more hour and at room temperature for another 2 h. Then, the solution was cooled in an ice bath and the reaction was quenched by the careful addition of water (7 mL). After the addition of aqueous hydrochloric acid and ethyl acetate (80 ml), the organic phase was separated, washed with brine, and dried (MgSO4). The solvent was evaporated to afford the title compound. Yield: 1.48 g (95% of theory); LC-MS (Method 4): tR=4.00 min; Mass spectrum (ESI+): m/z=446/448 (Br) [M+H]+.

Aufarbeitung

  1. customremained below 10° C
  2. temperatureThen, the solution was cooled in an ice bath
  3. customthe reaction was quenched by the careful addition of water (7 mL)
  4. additionAfter the addition of aqueous hydrochloric acid and ethyl acetate (80 ml)
  5. customthe organic phase was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-fd0cc4321c7f4e36b991d2753804575c
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08575157B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion