Réaction #1153995

Équation de réaction

3-[1-(t-Butoxycarbonyl)piperidin-2-yl]propanol

potassium t-butoxide

5-bromo-2-fluorobenzyl bromide

→

title intermediate

Rendement 50.0%

3-(5-bromo-2-fluorobenzyloxy)-1-[1-(t-butoxycarbonyl)piperidin-2-yl]propane

Rendement 50.0%

Solvants

tetrahydrofuran

methylene chloride

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Températurecooled to −78° C
2. 2
   TempératureThe resultant yellow reaction mixture was slowly warmed to 0° C.
3. 3
   workup.STIRRINGstirred for about four hours
4. 4
   Lavagewashed with 1 M potassium carbonate and brine
5. 5
   SéchageThe organic fraction was dried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo
8. 8
   AutreThe crude oil was purified by high performance liquid chromatography

Mode opératoire

3-[1-(t-Butoxycarbonyl)piperidin-2-yl]propanol (800 mg, 3.29 mmol) was taken up in tetrahydrofuran (17 ml), cooled to −40° C., and treated with potassium t-butoxide (1 M in tetrahydrofuran, 3.62 ml, 3.62 mmol). The resulting mixture was stirred at −40° C. for about 35 minutes, then cooled to −78° C. To this mixture was then added 5-bromo-2-fluorobenzyl bromide (881 mg, 3.29 mmol) as a solution in tetrahydrofuran (5 ml). The resultant yellow reaction mixture was slowly warmed to 0° C. and stirred for about four hours. The reaction mixture was diluted with methylene chloride and washed with 1 M potassium carbonate and brine. The organic fraction was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude oil was purified by high performance liquid chromatography, yielding 707 mg (50%) of the title intermediate as a clear oil.

Source