Bicarbonate Ion → HCID 11617867, Verbindung

HRID 2235264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2235264
Br[C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:6]1=[O:16].C([O-])([O-])=O.[Cs+].[Cs+].C(=O)(O)[O-]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:4]([C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:6]1=[O:16])[C:3]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:2]=1

Komponenten

5

Edukt 3

HCID 769Bicarbonate IonHCID 10796Cesium carbonateHCID 11632109HCID 11632109, Verbindung

Produkt 1

HCID 11617867HCID 11617867, VerbindungAusbeute 121,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator

Versuchsvorschrift

Charge a flask with 3-(2-bromo-6-chloro-benzyl)-1-cyclohexyl-pyrrolidin-2-one (Example 56) (250 mg, 0.67 mmol), Pd(dppf)Cl2 (54 mg, 0.067 mmol) and Cs2CO3 (660 mg, 2.0 mmol) and purge with nitrogen. Add DMF (6 mL) and water (0.6 mL) and stir. Add Bn-9-BBN (0.5 M, 4.0 mL, 2.0 mmol) and heat to 60° C. for 1 hour. Pour into saturated aqueous bicarbonate and extract with methylene chloride. Dry over sodium sulfate, filter and concentrate. Purify over silica gel (10% ethyl acetate in hexanes) to yield 155 mg (60%) of the title compound as a clear colorless oil. Mass spectrum (apci) m/z=382.3 (M+H).

Aufarbeitung

  1. custompurge with nitrogen
  2. extractionextract with methylene chloride
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify over silica gel (10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c8b3f0e00bfb4b2d9943539213be002b
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713979B2

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