Reaktion #90194

Reaktionsgleichung

DIAD

camphor sulfonic acid

8-Hydroxy-6,6-dimethyl-3-(2-phenyl-ethanesulfonyl)-5,6-dihydro-benzo[b]carbazol-11-one

[(4R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]methanol

PPh3

→

8-Isopropoxy-6,6-dimethyl-3-(2-phenyl-ethanesulfonyl)-5,6-dihydro-benzo[b]carbazol-11-one

Lösungsmittel

Ethyl acetate

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Filtrationthe reaction solution was filtered
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   SonstigeThe resulting residues were purified by silica gel column (ethyl acetate/hexane)
5. 5
   workup.DISSOLUTIONThe resulting residues were dissolved in THF (0.4 ml)
6. 6
   Sonstigeirradiation at 80° C. for 15 min under nitrogen atmosphere
7. 7
   WaschenThe organic layer was washed with saturated aqueous solution of sodium hydrocarbonate and saturated brine
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   SonstigeThe resulting residues were purified by thin layer chromatography (MeOH/DCM)
10. 10
    Sonstigeto obtain Compound GT20-2 (10.5 mg) and Compound GT20-3 (2.4 mg)

Vorschrift

8-Hydroxy-6,6-dimethyl-3-(2-phenyl-ethanesulfonyl)-5,6-dihydro-benzo[b]carbazol-11-one (30 mg, 0.0673 mmol), [(4R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]methanol (22.3 mg, 0.0808 mmol), and PPh3 (23 mg, 0.0875 mmol) were dissolved in THF (0.5 ml), added with DIAD (0.0169 ml, 0.0808 mmol), and the mixture was stirred at 50° C. overnight. After cooling, the reaction solution was filtered and concentrated under reduced pressure. The resulting residues were purified by silica gel column (ethyl acetate/hexane). The resulting residues were dissolved in THF (0.4 ml) and water (0.13 ml), added with camphor sulfonic acid (28.1 mg, 0.121 mmol), and then subjected to microwave irradiation at 80° C. for 15 min under nitrogen atmosphere. Ethyl acetate was added to the resultant. The organic layer was washed with saturated aqueous solution of sodium hydrocarbonate and saturated brine, and then concentrated under reduced pressure. The resulting residues were purified by thin layer chromatography (MeOH/DCM) to obtain Compound GT20-2 (10.5 mg) and Compound GT20-3 (2.4 mg).

Quelle