Hydrochloric Acid → tert-butyl (3S,4R)-4-amino-3-fluoropiperidine-1-carboxylate

HRID 1782013

Reaktionsgleichung

Reaktionsgleichung von HRID 1782013
C([NH:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C@H:10]1[F:22])C1C=CC=CC=1.Cl>CCO.[Pd]>[NH2:8][C@@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:11][C@@H:10]1[F:22]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 11312869cis-4-Benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidine

Produkt 1

HCID 11736104tert-butyl (3S,4R)-4-amino-3-fluoropiperidine-1-carboxylateAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of the enantiomeric mixture of cis-4-benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidine (prepared according to the procedures of J. Med. Chem. 1999, 42, 2087-2104, 1.0 g, 3.2 mmole) in EtOH (40 mL) was added 3 N HCl (2.5 L) and 10% Pd/C (50 mg). The reaction was shaken under H2 (40 psi) on a Parr apparatus for 14 h, then was filtered through Celite®. The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography on silica gel (10% MeOH/CHCl3) to afford the title compound (370 mg, 53%) as a white solid.

Aufarbeitung

  1. customprepared
  2. filtrationwas filtered through Celite®
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel (10% MeOH/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-22eb2861c23d43d680bdd14f2f88c5d2
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07498326B2

Verknüpfte Notizen

Wird geladen…