Morpholine → (R)-N-Boc-1-morpholino-2-propanamine

HRID 1670601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1670601
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:16])[CH2:10]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>C(#N)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH3:16])[CH2:10][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 8083MorpholineHCID 14427185(R)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonate

Produkt 1

HCID 57851166(R)-N-Boc-1-morpholino-2-propanamineAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Heat a mixture of (R)-methanesulfonic acid 2-tert-butoxycarbonylamino-propyl ester (0.083 mol, 20 g) and morpholine (0.83 mol, 72.2 g) in acetonitrile (210 mL) to 65° C. for 16 h. Concentrate the reaction mixture, dilute the residue with water, extract with dichloromethane, combine organic layer and wash with water. Dry the organic layer over anhydrous sodium sulfate, filter and concentrate under vacuum to obtain the title compound (12 g, 62%) as yellow thick oil. 1H NMR (400 MHz, CDCl3) δ 1.13 (d, 3H), 1.43 (s, 9H), 2.21 (dd, 1H), 2.26-2.32 (m, 1H), 2.35-2.39 (m, 2H), 2.48-2.55 (m, 2H), 3.63-3.70 (m, 5H), 4.68 (br s, 1H, —NH).

Aufarbeitung

  1. temperatureHeat
  2. concentrationConcentrate the reaction mixture
  3. additiondilute the residue with water
  4. extractionextract with dichloromethane
  5. washwash with water
  6. dry with materialDry the organic layer over anhydrous sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-cc610e987b104c01af76fa9e030e6186
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994164B2

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