2-Bromo-3-methoxypyridine → 2-(3-methoxy-2-pyridinyl)-5-phenylmethyl-(1S,4S)-2,5-diazabicyclo[2.2.1]-heptane

HRID 1031487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1031487
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:10]([N:17]1[CH2:22][C@@H:21]2[CH2:23][C@H:18]1[CH2:19][NH:20]2)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[CH3:9][O:8][C:7]1[C:2]([N:20]2[CH2:19][C@@H:18]3[CH2:23][C@H:21]2[CH2:22][N:17]3[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 903642-Bromo-3-methoxypyridineHCID 14612543(1S,4S)-2-Benzyl-2,5-Diazabicyclo[2.2.1]heptane

Produkt 1

HCID 186409522-(3-methoxy-2-pyridinyl)-5-phenylmethyl-(1S,4S)-2,5-diazabicyclo[2.2.1]-heptaneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-bromo-3-methoxy pyridine (9.9 g) and (1S,4S)-N-benzyl-2,5-diazabicyclo[2.2.1]heptane (10.9 g) was heated at 100° C. in a Parr bomb for 67 h. The reaction mixture was cooled to 23° C., dissolved in CH2Cl2, extracted with 5% NaHCO3, and finally wit:h H2O. The organic layer was dried over K2CO3, filtered, and concentrated under reduced pressure. The crude oil was purified by silica gel chromatography (CH2Cl2 :MeOH; 96:4) to give the desired product (7.93 g, 51%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 23° C.
  2. extractionextracted with 5% NaHCO3, and finally wit
  3. dry with materialThe organic layer was dried over K2CO3
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude oil was purified by silica gel chromatography (CH2Cl2 :MeOH; 96:4)

Quellen und Nachweise

ORD-Eintrag
ord-c33d51057ad54739892d9bc674b95593
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04954502

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