Reaktion #82352

Reaktionsgleichung

3(S)-(benzyloxyformamido)-1,2(S)-epoxy-4-phenylbutane

N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide

→

1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide

Ausbeute 92.7%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 10 hours
2. 2
   Sonstigethe solvent was then removed by evaporation
3. 3
   WaschenChromatography on silica gel using System H for the elution

Vorschrift

A solution of 2.98 g of 3(S)-(benzyloxyformamido)-1,2(S)-epoxy-4-phenylbutane and 2.1 g of N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide in 50 ml of ethanol was heated at reflux for 10 hours and the solvent was then removed by evaporation. Chromatography on silica gel using System H for the elution then gave 4.7 g of 1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide as a mixture of four diastereomers: MS: m/e 508 [M+H]+.

Quelle