Reaktion #557843

Reaktionsgleichung

ammonium chloride

Trans-4-aminocyclohexanol

compound

(3′S,4′R,7′S,8′S,8a′R)-6″-chloro-8′-(3-chloro-2-fluorophenyl)-4,4-dimethyl-3′,4′-diphenyl-3′,4′,8′,8a′-tetrahydro-1′H-dispiro[cyclohexane-1,6′-pyrrolo[2,1-c][1,4]oxazine-7′,3″-indole]-1′,2″(1″H)-dione

→

title compound

Ausbeute 101.1%

(4′S,5′R)-6″-chloro-4′-(3-chloro-2-fluorophenyl)-N-(trans-4-hydroxycyclohexyl)-1′-[(1R,2S)-2-hydroxy-1,2-diphenylethyl]-4,4-dimethyl-2″-oxo-1″,2″-dihydrodispiro[cyclohexane-1,2′-pyrrolidine-3′,3″-indole]-5′-carboxamide

Ausbeute 101.1%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux for 6 days
3. 3
   TemperaturAfter cooling
4. 4
   Extraktionfollowed by extraction with ethyl acetate
5. 5
   WaschenThe organic layer was washed with brine
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   SonstigeThe solvent was evaporated under reduced pressure
8. 8
   Sonstigethe residue was purified by silica gel column chromatography [chloroform:methanol=100:0→30:1 (v/v)]

Vorschrift

Trans-4-aminocyclohexanol (167 mg, 1.45 mmol) was added to a tetrahydrofuran (10 ml) solution of the compound (194 mg, 0.29 mmol) obtained in Step 1 above and the resulting mixture was heated to reflux for 6 days. After cooling, saturated ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [chloroform:methanol=100:0→30:1 (v/v)] to give 230 mg (100%) of the title compound as a pale yellow amorphous solid.

Quelle