Ethanol → HCID 69817666, Verbindung

HRID 2417410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2417410
[CH2:1]([N:8](C(O)CCC1C=CC([N+]([O-])=O)=CC=1)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[Cl-].[NH4+:35].[CH2:36]([OH:38])[CH3:37]>[Fe]>[NH2:35][C:5]1[CH:6]=[CH:7][C:2]([CH2:1][C@H:37]([N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:36][OH:38])=[CH:3][CH:4]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 86591183HCID 86591183, Verbindung

Produkt 1

HCID 69817666HCID 69817666, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23925IronKatalysator

Versuchsvorschrift

To a suspension of (2S)-2-[(N-benzyl-N-((2S)-2-hydroxy-3-phenoxypropyl]amino]-3-(4-nitrophenyl)-1-propanol (1.12 g) in ethanol (11 ml)—water (2.2 ml) were added powdered iron (573 mg) and ammonium chloride (55 mg). The mixture was gently heated to reflux for 1 hour and allowed to cool to room temperature. After the insoluble material was filtered off, the filtrate was concentrated and partitioned between chloroform and water. The organic layer was separated, washed successively with water and brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate) to give (2S)-3-(4-aminophenyl)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-1-propanol (990 mg) as a pale yellow oil.

Aufarbeitung

  1. temperatureThe mixture was gently heated
  2. temperatureto reflux for 1 hour
  3. filtrationAfter the insoluble material was filtered off
  4. concentrationthe filtrate was concentrated
  5. custompartitioned between chloroform and water
  6. customThe organic layer was separated
  7. washwashed successively with water and brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-41d7adc3ff60447296ec2d93e77947da
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06826033B2

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