StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Triphenylphosphine → (2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl)propan-2-ol

HRID 2421012
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2421012
[N:1]([CH2:4][C@@H:5]([OH:22])[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:9][CH2:8]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[NH2:1][CH2:4][C@@H:5]([OH:22])[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:9][CH2:8]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 59295965(2S)-1-azido-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propan-2-ol

Produkt 1

HCID 11151315(2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl)propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

The oil from Step 2 was dissolved in wet tetrahydrofuran (225 mL) and was treated with triphenylphosphine (53.3 g). The reaction was heated at 60° C. and stirred for 4 h. The solvent was removed under vacuum, the residue redissolved into 2N hydrochloric acid (1 L) and the aqueous layer was extracted with ethyl acetate (3×700 mL). The aqueous phase was basified with aqueous 2 N sodium hydroxide solution and extracted with DCM (3×1 L). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under vacuum. The crude material was purified by chromatography (8% 7N ammonia in methanol/DCM) to give the title compound as a yellow oil (17 g).

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue redissolved into 2N hydrochloric acid (1 L)
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×700 mL)
  4. extractionextracted with DCM (3×1 L)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe crude material was purified by chromatography (8% 7N ammonia in methanol/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-bd6f2005c6d64a60a5bec0b6a64cb27d
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07956070B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion