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1-Benzyl-4-(N-tert-butoxycarbonyl-N-isopropylamino)piperidine → tert-butyl N-(piperidin-4-yl)-N-(propan-2-yl)carbamate

HRID 1662108
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1662108
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:15]([CH3:17])[CH3:16])[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[C:21]([O:20][C:18]([N:14]([CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH:15]([CH3:17])[CH3:16])=[O:19])([CH3:23])([CH3:24])[CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 674284161-Benzyl-4-(N-tert-butoxycarbonyl-N-isopropylamino)piperidine

Produkt 1

HCID 50986573tert-butyl N-(piperidin-4-yl)-N-(propan-2-yl)carbamateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A solution of 1-benzyl-4-(N-tert-butoxycarbonyl-N-isopropylamino)piperidine (79.0 g, 0.24 mol) in ethanol (140 mL) was flushed with nitrogen for 15 minutes. This solution was then added to a 2 L Parr flask containing a mixture of 10% palladium on carbon (15.8 g; ca. 50% wt. water) in ethanol (100 mL), which solution had been flushed with nitrogen for 15 minutes. This reaction mixture was placed on a Parr Shaker under hydrogen at 50 psi for 24 hours. The reaction mixture was filtered through a pad of Celite and the Celite washed with ethanol. The filtrate was then concentrated in vacuo to afford 57.0 g of the title intermediate as a white solid (>99% yield).

Aufarbeitung

  1. additionThis solution was then added to a 2 L Parr flask
  2. additioncontaining
  3. customhad been flushed with nitrogen for 15 minutes
  4. filtrationThe reaction mixture was filtered through a pad of Celite
  5. washthe Celite washed with ethanol
  6. concentrationThe filtrate was then concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-aa206e3d9f604a8fb0982103b3f3670c
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08030502B2

Notizen zur Reaktion

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