Potassium Carbonate → Tert-butyl 4-(((benzyloxy)carbonyl)(ethyl)amino)piperidine-1-carboxylate

HRID 1193413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1193413
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9](Cl)=[O:10])=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[CH2:19]([NH:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1)[CH3:20].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH2:7]([O:8][C:9]([N:21]([CH2:19][CH3:20])[CH:22]1[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[CH2:26][CH2:27]1)=[O:10])[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 18374730tert-Butyl 4-(ethylamino)piperidine-1-carboxylateHCID 86663382Cbz-Cl toluene

Produkt 1

HCID 18677722Tert-butyl 4-(((benzyloxy)carbonyl)(ethyl)amino)piperidine-1-carboxylateAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A 50% Cbz-Cl-toluene solution (20.87 ml, 61.40 mmol, 2.0 eq) was added dropwise at 0° C. to a mixture of tert-butyl 4-(ethylamino)piperidine-1-carboxylate (7.0 g, 30.70 mmol, 1.0 eq) and K2CO3 (12.71 g, 92.10 mmol, 3.0 eq) in DCM (100 ml) and the mixture was stirred for 14 hours at RT. The reaction mixture was diluted with DCM (200 ml), washed with water (100 ml) and sat. NaCl solution (100 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 20% ethyl acetate in hexane). Yield: 63% (7.0 g, 19.33 mmol)

Aufarbeitung

  1. washwashed with water (100 ml) and sat. NaCl solution (100 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column chromatography (silica gel, 20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-941621b5e21f455ab798c88bc2dc1798
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680159B2

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