Triphenylphosphine → 4-Amino-1-(p-nitrobenzyloxycarbonyl)-piperidine

HRID 891714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891714
[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(#N)C>[NH2:1][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 62649Sodium sulfate decahydrateHCID 222427144-Azido-1-(p-nitrobenzyloxycarbonyl)piperidine

Produkt 1

HCID 222428434-Amino-1-(p-nitrobenzyloxycarbonyl)-piperidineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 4-azido-1-(p-nitrobenzyloxycarbonyl)-piperidine (2.81 g, 9.17 mmol) (obtained as described in Reference Example 51(3)) in acetonitrile (84 ml) was added triphenylphosphine (2.53 g, 9.63 mmol), and the mixture was stirred in an oil bath (70° C.) for 3 hours. After checking the completion of the reaction, sodium sulfate decahydrate (3.10 g, 9.63 mmol) was added thereto and the reaction mixture was stirred for 3 hours. After checking the completion of the reaction, the reaction mixture was filtered and partitioned between methylene chloride and 0.1M aqueous hydrogen chloride solution. To the obtained aqueous layer were added methylene chloride and sodium hydrogencarbonate, and the aqueous layer was extracted with methylene chloride. The obtained organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was dried under reduced pressure to give 4-amino-1-(p-nitrobenzyloxycarbonyl)-piperidine (2.33 g, yield 91%) as pale yellow crystals.

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction mixture was stirred for 3 hours
  3. customthe completion of the reaction
  4. filtrationthe reaction mixture was filtered
  5. custompartitioned between methylene chloride and 0.1M aqueous hydrogen chloride solution
  6. additionTo the obtained aqueous layer were added methylene chloride and sodium hydrogencarbonate
  7. extractionthe aqueous layer was extracted with methylene chloride
  8. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8169dd54444b4c67b565ae1632fba091
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001897B2

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