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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 406781
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 406781
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
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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-d78ee5b2f37a415d8304824e7d342e87
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08754076B2

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