Reaktion #440554

Reaktionsgleichung

(+/−)-(1R*,2R*,3R*,4S*,6S*)-3-benzyloxycarbonylamino-tricyclo[2.2.1.02,6]heptane-1,3-dicarboxylic acid dimethyl ester

methanol

HCl

→

title compound

Ausbeute 64.7%

(1R*,2R*,3R*,4S*,6S*)-3-Benzyloxycarbonylamino-tricyclo[2.2.1.02,6]heptane-1,3-dicarboxylic acid

Ausbeute 64.7%

Lösungsmittel

tetrahydrofuran

sodium hydroxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe solution was refluxed under nitrogen for 15 hours
2. 2
   Extraktionextracted with ethyl acetate (2×200 mL)
3. 3
   WaschenThe extract was washed with 200 mL portions of water and saturated brine
4. 4
   Trocknendried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuum
7. 7
   SonstigeThe resulting residue was recrystallized from ethyl acetate/hexane

Vorschrift

A suspension of 2.0 g (5.6 mmole) of (+/−)-(1R*,2R*,3R*,4S*,6S*)-3-benzyloxycarbonylamino-tricyclo[2.2.1.02,6]heptane-1,3-dicarboxylic acid dimethyl ester in a mixture of 30 mL of tetrahydrofuran and 30 mL of 1 N aqueous sodium hydroxide was stirred at room temperature for 24 hours. Because the starting material was unchanged, methanol was added until homogeneity was achieved and the solution was refluxed under nitrogen for 15 hours. The mixture was acidified with concentrated HCl and extracted with ethyl acetate (2×200 mL). The extract was washed with 200 mL portions of water and saturated brine, dried over sodium sulfate, filtered and concentrated in vacuum. The resulting residue was recrystallized from ethyl acetate/hexane to give 1.2 g of the title compound as a white solid, m.p. 205° C.

Quelle