Carbon Tetrachloride → HCID 57779814, Verbindung

HRID 552906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 552906
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH:13](O)[CH2:12][CH:11]3[O:16][C:17](=[O:19])[CH:18]=[C:10]23)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:40]>C(#N)C.ClCCl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH:13]([Cl:40])[CH2:12][CH:11]3[O:16][C:17](=[O:19])[CH:18]=[C:10]23)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 57779818HCID 57779818, Verbindung

Produkt 1

HCID 57779814HCID 57779814, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

At 70° C., 146.0 mg (0.52 mmol) of 4-[(6-chloropyridin-3-yl)methyl]-6-hydroxy-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one (cf. I-16) and 274.2 mg (1.05 mmol) of triphenylphosphine are stirred in a mixture of 2.5 ml of acetonitrile and 2.5 ml of carbon tetrachloride. After cooling to room temperature, the mixture is diluted with dichloromethane and washed successively with dilute aqueous ammonium hydroxide solution and saturated sodium chloride solution: the organic phase is dried over sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 063 m) using the mobile phase ethyl acetate and subsequent preparative HPLC gives both possible diastereomers of 4-[(6-chloropyridin-3-yl)methyl]-6-chloro-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one: (a) 4 mg of diastereomer A (3% of theory) and (b) 15 mg of diastereomer B (9% of theory). In addition, (c) 10 mg (7% of theory) of 4-[(6-chloropyridin-3-yl)methyl]-7,7a-dihydrofuro[3,2-b]pyridin-2(4H)-one are obtained.

Aufarbeitung

  1. washwashed successively with dilute aqueous ammonium hydroxide solution and saturated sodium chloride solution
  2. dry with materialthe organic phase is dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 063 m)

Quellen und Nachweise

ORD-Eintrag
ord-b1c7f56436544b62ba3485e7073e3bba
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951951B2

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