(Diethylamino)sulfur trifluoride → [1-(2-Fluoro-propyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 1257746Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257746
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15](O)[CH3:16])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:25])CC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([F:25])[CH3:16])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 56973353tert-Butyl (1-(2-hydroxypropyl)piperidin-4-yl)carbamate

Produkt 1

HCID 67323267[1-(2-Fluoro-propyl)-piperidin-4-yl]-carbamic acid tert-butyl esterAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a cold solution of [1-(2-hydroxy-propyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.70 g, 2.7 mmol) in DCM (30 mL) was added DAST (1.1 mL, 8.1 mmol) and the mixture was stirred at 25° C. for 20 h. The reaction mixture was washed with saturated sodium bicarbonate solution, water, brine, dried over Na2SO4 and concentrated under reduced pressure to afford [1-(2-fluoro-propyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.5 g, 70%). LCMS (Method G; ESI): RT=0.53 min; m+1=261.3. This was used without further purification below.

Aufarbeitung

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution, water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b6ca3cd3ab1f4e64b0922080fa17e1c3
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461328B2

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