Lithium tri-s-butylborohydride → HCID 86691846, Verbindung

HRID 1616232Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616232
[Br:1][C:2]1[CH:3]=[C:4](/[C:10](=[N:12]/[S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])/[CH3:11])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C@H:10]([NH:12][S:13]([C:15]([CH3:16])([CH3:18])[CH3:17])=[O:14])[CH3:11])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Komponenten

5

Edukt 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 89735588HCID 89735588, Verbindung

Produkt 1

HCID 86691846HCID 86691846, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 38-1 (500 mg, 1.5 mmol) in THF (4 mL) at −78 C was added L-Selectride (3.1 mL, 3.1 mmol, 1M). After 10 minutes, the reaction was diluted in EtOAc, washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered and concentrated. Purification by reverse phase chromatography (1-100%, 0.1% TFA in H2O/Acetonitrile) gave desired product. MS (M+H)+: observed=329.0/331.0, calculated=329.3/331.3.

Aufarbeitung

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by reverse phase chromatography (1-100%, 0.1% TFA in H2O/Acetonitrile)

Quellen und Nachweise

ORD-Eintrag
ord-50c28bc851004b429d62911ffcb29678
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765784B2

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