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1-Phenethylamine, (+)- → rel-1-(1,1-Dimethylethyl) 3-methyl (3R,5S)-1,3,5-piperidinetricarboxylate

HRID 1259874
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1259874
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:11][CH:10]([C:18]([OH:20])=[O:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1([C@H](N)C)C=CC=CC=1>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:11][C@H:10]([C:18]([OH:20])=[O:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 6431891-Phenethylamine, (+)-HCID 232911511-((Tert-butoxy)carbonyl)-5-(methoxycarbonyl)piperidine-3-carboxylic acid

Produkt 1

HCID 11358159rel-1-(1,1-Dimethylethyl) 3-methyl (3R,5S)-1,3,5-piperidinetricarboxylateAusbeute 14,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of (3RS,5SR)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)piperidine-3-carboxylic acid (6.16 g), (R)-(+)-1-phenylethylamine (2.60 g) and ethanol (24 ml) was dissolved by heating to 70° C., and recrystallized. The precipitated crystals were collected by filtration, dissolved in ethanol (7 ml) again and recrystallized. The precipitated crystals were collected by filtration, the obtained crystals were suspended in water, acidified by adding saturated aqueous potassium hydrogen sulfate solution, and the mixture was extracted 3 times with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (915 mg) as a powder.

Aufarbeitung

  1. dissolutionwas dissolved
  2. customrecrystallized
  3. filtrationThe precipitated crystals were collected by filtration
  4. dissolutiondissolved in ethanol (7 ml) again
  5. customrecrystallized
  6. filtrationThe precipitated crystals were collected by filtration
  7. additionby adding saturated aqueous potassium hydrogen sulfate solution
  8. extractionthe mixture was extracted 3 times with ethyl acetate
  9. washThe extract was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f7cc1ce8b7994004bae695145ad89763
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08466282B2

Notizen zur Reaktion

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