Triethylamine → 4-t-Butylsulfinylamino-1-ethoxycarbonyl piperidine

HRID 915001

Reaktionsgleichung

Reaktionsgleichung von HRID 915001
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:20]([S:24](Cl)=[O:25])([CH3:23])([CH3:22])[CH3:21]>ClCCl>[C:20]([S:24]([NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1)=[O:25])([CH3:23])([CH3:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 46868612-Methylpropane-2-sulfinyl chloride

Produkt 1

HCID 227477804-t-Butylsulfinylamino-1-ethoxycarbonyl piperidineAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Ethyl 4-amino-1-piperidinecarboxylate (300 mg) and triethylamine (258 mg) were dissolved in 5 ml of dichloromethane. To the mixture, 2 ml of solution of t-butylsulfinyl chloride (222 mg) in dichloromethane was added and the mixture was stirred at room temperature for 4 hours. The solution was partitioned into an aqueous solution of potassium hydrogen sulfate and ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate anhydride. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography to give 378 mg of 4-t-butylsulfinylamino-1-ethoxycarbonyl piperidine.

Aufarbeitung

  1. customThe solution was partitioned into an aqueous solution of potassium hydrogen sulfate and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate anhydride
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e0e5ee92ade94cb5aacd46048f215161
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265130B2

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