Réaction #1154018

Équation de réaction

sodium hydride

Sodium iodide

3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl bromide

2-fluoro-5-bromobenzyl alcohol

→

1-[2-fluoro-5-bromobenzyloxy]-3-[1-(t-butoxycarbonyl)piperidin-3-yl]propane

Solvants

N,N-dimethylformamide

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture was partitioned between 1 M potassium carbonate and methylene chloride
2. 2
   ExtractionThe aqueous fraction was back extracted with methylene chloride
3. 3
   Séchagedried over sodium sulfate
4. 4
   AutreThe solvents were removed in vacuo
5. 5
   AutreThe desired title product was further purified by liquid chromatography

Mode opératoire

An amount of 3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl bromide (180 mg, 0.588 mmol) was dissolved in N,N-dimethylformamide (1.5 ml) in a 10 ml flask under a nitrogen atmosphere. Sodium iodide (176 mg, 1.18 mmol) was added at ambient temperature, and the resulting mixture was stirred for ten minutes. The reaction mixture was treated with 2-fluoro-5-bromobenzyl alcohol (121 mg, 0.588 mmol), delivered as a solution in 0.5 ml of N,N-dimethylformamide. To this mixture was then added sodium hydride (60%, 35 mg, 0.882 mmol) and the resulting mixture was stirred at ambient temperature for three hours. The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was partitioned between 1 M potassium carbonate and methylene chloride. The aqueous fraction was back extracted with methylene chloride. The organic fractions were combined, and dried over sodium sulfate. The solvents were removed in vacuo. The desired title product was further purified by liquid chromatography.

Source