Reaktion #543193

Reaktionsgleichung

5-nitro-2-(2,2,6,6-tetramethyl-1,1-dioxo-1,2,3,6-tetrahydro-1λ6-thiopyran-4-yl)-pyridine

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title compound

Ausbeute 64.0%

6-(2,2,6,6-Tetramethyl-1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-pyridin-3-ylamine

Ausbeute 64.0%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered through Celite
2. 2
   Waschenthe filter cake was washed with MeOH
3. 3
   SonstigeThe solvents were evaporated in vacuo
4. 4
   SonstigeThe residue was purified on a 25-g Sepra Si 50 SPE column (Isco system
5. 5
   workup.WAIT10-50% EtOAc-hexane for 5-30 min
6. 6
   workup.WAIT50-65% EtOAc-hexane over 40 min

Vorschrift

A solution of 5-nitro-2-(2,2,6,6-tetramethyl-1,1-dioxo-1,2,3,6-tetrahydro-1λ6-thiopyran-4-yl)-pyridine (322 mg, 1.04 mmol, as prepared in the previous step) in MeOH (10 mL) was hydrogenated with 5% Pd/C and 1 atm H2 at RT for 17 h. The mixture was filtered through Celite, and the filter cake was washed with MeOH. The solvents were evaporated in vacuo. The residue was purified on a 25-g Sepra Si 50 SPE column (Isco system: Flow rate=20 mL/min; Eluent=10% EtOAc-hexane for 0-3 min, then 10-50% EtOAc-hexane for 5-30 min, then 50-65% EtOAc-hexane over 40 min, then 65-100% EtOAc-hexane over 40 min) to afford the title compound (187 mg, 64%) as an off-white solid. Mass spectrum (ESI, m/z): Calcd. for C14H22N2O2S, 283.1 (M+H), found 283.1.

Quelle