Potassium;tri(butan-2-yl)boranuide → HCID 69890897, Verbindung

HRID 2088110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2088110
CCC(C)[BH-](C(C)CC)C(C)CC.[K+].[C:15]([C@@H:17]1[C@:23]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:24]([CH2:25][CH:26]=[CH2:27])[C@H:19]([CH:20]=[CH:21][C:22]2=[O:34])[CH2:18]1)#[N:16]>C1COCC1>[C:15]([C@@H:17]1[C@:23]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:24]([CH2:25][CH:26]=[CH2:27])[C@@H:19]([CH2:20][CH2:21][C@H:22]2[OH:34])[CH2:18]1)#[N:16]

Komponenten

4

Edukt 2

HCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 69889607HCID 69889607, Verbindung

Produkt 1

HCID 69890897HCID 69890897, VerbindungAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of K-Selectride® in THF (1M, 6.5 ml, 6.5 mmol) was added dropwise to a stirred solution of (1R*,5S*,7S*)-7-cyano-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]oct-3-en-2-one (Description 23c; 295 mg, 1.11 mmol) in THF (7 ml) at −78° C. The reaction mixture was slowly warm up to +15° C. over 6 hours and carefully quenched with a mixture of 2M NaOH (8 ml) and H2O2 (35%, 2 ml). The mixture was stirred for 20 minutes. The mixture was treated with saturated aqueous Na2SO3 and extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate) to give the title compound (50 mg, 17%).

Aufarbeitung

  1. temperatureThe reaction mixture was slowly warm up to +15° C. over 6 hours
  2. customcarefully quenched with a mixture of 2M NaOH (8 ml) and H2O2 (35%, 2 ml)
  3. additionThe mixture was treated with saturated aqueous Na2SO3
  4. extractionextracted into dichloromethane
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-28b3c710756042fb9c0aeb8facb00648
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727249B2

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