Tert-butyl 3-(tert-butylcarbamoyl)piperazine-1-carboxylate → 1-Piperazinecarboxamide

HRID 466877

Reaktionsgleichung

Reaktionsgleichung von HRID 466877
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10](C(NC(C)(C)C)=O)[CH2:9]1)=O)(C)(C)C.C(OC([NH:31][C@@H](CC1C=CC=CC=1)[C@@H]1OC1)=O)C1C=CC=CC=1>C(O)(C)C>[N:8]1([C:6]([NH2:31])=[O:5])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1

Komponenten

4

Edukt 2

HCID 4063013Tert-butyl 3-(tert-butylcarbamoyl)piperazine-1-carboxylateHCID 9861019(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

Produkt 1

HCID 2581921-Piperazinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

0.395 g of 4-(tert.butoxycarbonyl)-N-tert.butyl-2-piperazinecarboxamide was dissolved in 50 ml of dry isopropanol and treated with 0.413 g of 3(S)-(benzyloxyformamido)-1,2(S)-epoxy-4-phenylbutane. The mixture was stirred at room temperature for 72 hours. The solvent was removed by evaporation to give a brown semi-solid material which was purified by flash chromatography on silica gel using 5% methanol in dichloromethane for the elution. There was obtained 0.234 g of 1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-4-(tert.butoxycarbonyl)-N-tert.butyl-2(R or S)-piperazinecarboxamide as a mixture of diastereomers.

Aufarbeitung

  1. customThe solvent was removed by evaporation
  2. customto give a brown semi-solid material which
  3. customwas purified by flash chromatography on silica gel using 5% methanol in dichloromethane for the elution

Quellen und Nachweise

ORD-Eintrag
ord-fc0eb75fafce4aba83baeacdccbecccf
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05157041

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