Borane → HCID 67043493, Verbindung

HRID 1907265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1907265
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:24])[CH2:12][CH:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][C:15](O)=[O:16])[CH3:9])=[CH:4][CH:3]=1.B>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][C:11](=[O:24])[CH2:12][CH:13]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:14][CH2:15][OH:16])[CH3:9])=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 6331BoraneHCID 67043470HCID 67043470, Verbindung

Produkt 1

HCID 67043493HCID 67043493, VerbindungAusbeute 102,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5-((S)-1-(4-bromophenyl)ethylamino)-5-oxo-3-phenylpentanoic acid (1.92 g, 4.92 mmol, 1.0 equiv) was dissolved in THF (30 mL) and the resulting solution cooled to 0° C. Borane (1.0 M in THF, 10.5 mL, 10.5 mmol, 2.1 equiv) was added via syringe. After 0.5 h LC-MS showed formation of the alcohol. The excess borane was quenched by the drop-wise addition of 1.0 M aq HCl and the mixture was transferred to a separatory funnel. The layers were separated and the organic layer washed with brine, dried over Na2SO4, filtered and evaporated. The resulting N—((S)-1-(4-bromophenyl)ethyl)-5-hydroxy-3-phenylpentanamide (˜1.9 g, >95% yield) was of sufficient purity to use in the next step.

Aufarbeitung

  1. customThe excess borane was quenched by the drop-wise addition of 1.0 M aq HCl
  2. customthe mixture was transferred to a separatory funnel
  3. customThe layers were separated
  4. washthe organic layer washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a32f90095f7348abbbf0e25cf2749602
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598160B2

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