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Water → Tert-butyl 4-(aminomethyl)-4-benzylsulfanylpiperidine-1-carboxylate

HRID 453582
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 453582
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([S:14][C:15]1([CH2:28][N+:29]([O-])=O)[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>C(OCC)C.O1CCCC1.C(OCC)(=O)C>[NH2:29][CH2:28][C:15]1([S:14][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 962WaterHCID 21226445Aluminium lithium hydride2×HCID 57475998Tert-butyl 4-(benzylthio)-4-(nitromethyl)piperidine-1-carboxylate

Produkt 1

HCID 57475999Tert-butyl 4-(aminomethyl)-4-benzylsulfanylpiperidine-1-carboxylateAusbeute 28,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283
Diethyl Ether
Lösungsmittel
2×
HCID 8028TetrahydrofuranLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a mixture of lithium aluminum hydride (0.4 g) and diethyl ether (20 mL) was added a solution of tert-butyl 4-(benzylthio)-4-(nitromethyl)piperidine-1-carboxylate (1.28 g) in diethyl ether (5 mL) at 0° C. The reaction mixture was heated under reflux for 1 hr. Ethyl acetate was added to decompose excess lithium aluminum hydride, and then water was added. The reaction mixture was diluted with a mixed solvent of tetrahydrofuran and ethyl acetate, and the inorganic salt was removed by filtration. The filtrate was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (0.33 g, yield 28%) as a colorless oil from a fraction eluted with ethyl acetate-methanol (2:1, volume ratio).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 hr
  3. customthe inorganic salt was removed by filtration
  4. washThe filtrate was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c751a4213cf74a9391817d1ab0f908bf
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492405B2

Notizen zur Reaktion

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