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Hydrochloric Acid → tert-Butyl (3R)-3-(aminomethyl)piperidine-1-carboxylate

HRID 272097
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 272097
[N:1]([CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>O1CCCC1>[NH2:1][CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 10083012(S)-Tert-butyl 3-(azidomethyl)piperidine-1-carboxylate

Produkt 1

HCID 1502023tert-Butyl (3R)-3-(aminomethyl)piperidine-1-carboxylateAusbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 600 mg of (3S)-3-azidomethyl-1-(tert-butoxycarbonyl)piperidine in 12.5 ml of 20% hydrous tetrahydrofuran, 622 mg of triphenylphosphine was added at room temperature, followed by 45 minutes' refluxing under heating. The reaction liquid was rendered acidic by addition of 0.5 N hydrochloric acid, and successively washed with chloroform and ethyl acetate. Then 4N aqueous sodium hydroxide solution was added to the aqueous layer to render the latter basic, followed by extraction with chloroform and drying over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, 497 mg of the title compound was obtained.

Aufarbeitung

  1. temperature' refluxing
  2. temperatureunder heating
  3. customThe reaction liquid
  4. washsuccessively washed with chloroform and ethyl acetate
  5. additionThen 4N aqueous sodium hydroxide solution was added to the aqueous layer
  6. extractionfollowed by extraction with chloroform
  7. dry with materialdrying over anhydrous sodium sulfate
  8. distillationDistilling the solvent off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-607e516fc46f44798928a6187dc4c104
Quelldatensatz
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07452908B2

Notizen zur Reaktion

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