Reaktion #453672

Reaktionsgleichung

N-benzyloxy-4-tert-butoxycarbonyl-1-[4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine-1-sulfonyl]piperazine-2-(R)-carboxamide

trifluoroacetic acid

→

N-benzyloxy-1-[4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine-1-sulfonyl]piperazine-2-(R)-carboxamide

Ausbeute 99.6%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated in vacuo
2. 2
   Sonstigepartitioned between ethyl acetate (500 ml) and sat. sodium bicarbonate (200 ml)
3. 3
   WaschenThe aqueous layer was washed with ethyl acetate
4. 4
   Trocknenthe combined organic layers were dried over MgSO4
5. 5
   Einengenconcentrated in vacuo
6. 6
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (40 ml)
7. 7
   workup.ADDITIONslowly added to hexane (200 ml) with vigorous stirring
8. 8
   FiltrationThe resulting slurry was filtered

Vorschrift

To a solution of N-benzyloxy-4-tert-butoxycarbonyl-1-[4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine-1-sulfonyl]piperazine-2-(R)-carboxamide (24.40 g, 36.40 mmol) [prepared as described in Step 4 above] in methylene chloride (90 ml) was added trifluoroacetic acid (60 ml). The reaction mixture was stirred for 2 h, concentrated in vacuo, and partitioned between ethyl acetate (500 ml) and sat. sodium bicarbonate (200 ml). The aqueous layer was washed with ethyl acetate and the combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was dissolved in ethyl acetate (40 ml) and slowly added to hexane (200 ml) with vigorous stirring. The resulting slurry was filtered to afford 20.65 g of N-benzyloxy-1-[4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine-1-sulfonyl]piperazine-2-(R)-carboxamide as a white solid.

Quelle