2-Chloroethanol → 2-chloro-5-(2-chloroethoxy)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 2085640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2085640
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:42][CH2:43][CH2:44]O.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([O:22][CH2:44][CH2:43][Cl:42])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]3)[CH2:15]1)[CH2:9]2)=[O:5]

Komponenten

6

Edukt 4

HCID 342-ChloroethanolHCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 227314932-Chloro-5-hydroxy-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Produkt 1

HCID 227314842-chloro-5-(2-chloroethoxy)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-5-hydroxy-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (WO 99/29661) (0.30 g), triphenylphosphine (0.25 g) and 2-chloroethanol (0.07 ml) in tetrahydrofuran (4 ml) was added diethyl azodicarboxylate (0.15 ml) and the reaction mixture stirred at room temperature for 18 h. Further triphenylphosphine (0.12 g) and diethyl azodicarboxylate (0.08 ml) were added and the reaction stirred for an additional 4 h. Silica was added and the reaction mixture concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluting with 20% ethyl acetate in isohexanes) to deliver the sub-title compound as a lightly coloured oil (0.31 g).

Aufarbeitung

  1. stirringthe reaction stirred for an additional 4 h
  2. additionSilica was added
  3. concentrationthe reaction mixture concentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (eluting with 20% ethyl acetate in isohexanes)

Quellen und Nachweise

ORD-Eintrag
ord-565e0fe952d54fc8baf6698f3409b4a4
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06720452B2

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