Reacción #48168

Ecuación de reacción

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

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe mixture was evaporated to dryness
2. 2
   workup.DISSOLUTIONdissolved in tert-butylmethylether
3. 3
   LavadoThe organic phase was washed with 0.5M sodium hydroxide solution and 5% sodium chloride solution
4. 4
   Secadodried over sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated to dryness
7. 7
   OtroThe product was recrystallized from methanol
8. 8
   Otroto yield 9.498 g (88%) as white crystals

Procedimiento

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%).

Fuente