Réaction #48168

Équation de réaction

Diisopropyl azodicarboxylate

3-methyl-4-nitrophenol

1-tert-butyloxycarbonyl-4-hydroxy-piperidine

triphenylphosphine

→

4-(3-Methyl-4-nitro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Autrethe mixture was evaporated to dryness
2. 2
   workup.DISSOLUTIONdissolved in tert-butylmethylether
3. 3
   LavageThe organic phase was washed with 0.5M sodium hydroxide solution and 5% sodium chloride solution
4. 4
   Séchagedried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated to dryness
7. 7
   AutreThe product was recrystallized from methanol
8. 8
   Autreto yield 9.498 g (88%) as white crystals

Mode opératoire

Diisopropyl azodicarboxylate (10.56 mL, 1.6 eq.) was added to a cold (0° C.) mixture of 3-methyl-4-nitrophenol (5 g, 1.0 eq.), 1-tert-butyloxycarbonyl-4-hydroxy-piperidine (9.96 g, 1.6 eq.) and triphenylphosphine (13.85 g, 1.6 eq.) in tetrahydrofuran (205 mL). After 1 h stirring, the mixture was evaporated to dryness and dissolved in tert-butylmethylether. The organic phase was washed with 0.5M sodium hydroxide solution and 5% sodium chloride solution, dried over sodium sulfate, filtered and evaporated to dryness. The product was recrystallized from methanol to yield 9.498 g (88%) as white crystals. MS (m/e): 336.2 (M, 10%).

Source