Cyclopropylamine → [(R)-1-(5-Bromo-pyridin-2-yl)-pyrrolidin-3-yl]-cyclopropyl-amine

HRID 423403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423403
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH2:11][C@H:10](OS(C)(=O)=O)[CH2:9]2)=[N:6][CH:7]=1.[CH:18]1([NH2:21])[CH2:20][CH2:19]1>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH2:11][C@@H:10]([NH:21][CH:18]3[CH2:20][CH2:19]3)[CH2:9]2)=[N:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 69828CyclopropylamineHCID 86638154methanesulfonic acid (S)-1-(5-bromo-pyridin-2-yl)-pyrrolidin-3-yl ester

Produkt 1

HCID 66673109[(R)-1-(5-Bromo-pyridin-2-yl)-pyrrolidin-3-yl]-cyclopropyl-amineAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Dissolve methanesulfonic acid (S)-1-(5-bromo-pyridin-2-yl)-pyrrolidin-3-yl ester (3.07 g, 9.48 mmol) and cyclopropylamine (1.7 mL, 23.68 mmol) in THF (20 mL). Microwave the mixture at 130° C. for 6 h. Dilute the mixture with EtOAc (100 mL) and wash with saturated NaHCO3 (25 mL). Dry the organic portion over Na2SO4, filter, and concentrate. Purify the crude material by chromatography, eluting with a gradient of 75-100% EtOAc/hexane to give 1.638 g (61%) of the title compound. LC-MS/ES m/z (79Br) 283.0 [M+H]+.

Aufarbeitung

  1. washwash with saturated NaHCO3 (25 mL)
  2. dry with materialDry the organic portion over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the crude material by chromatography
  6. washeluting with a gradient of 75-100% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-745b8b3e18d846b79c855d0f8f90b2f4
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101764B2

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