Trifluoroacetic acid → 1-[2-Fluoro-5-bromobenzyloxy]-3-(piperidin-3-yl)propane

HRID 1066837Notes

Reaction equation

FC(F)(F)C(O)=O.[F:8][C:9]1[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][C:10]=1[CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]1>C(Cl)Cl>[F:8][C:9]1[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][C:10]=1[CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1

Participants

Conditions

Temperature: 0 °C

Procedure

In a 100 ml round bottom flask, 1-[2-fluoro-5-bromobenzyloxy]-3-[1-(t-butoxycarbonyl)piperidin-3-yl]propane (0.395 g) was dissolved in methylene chloride (4.2 ml). The solution was cooled to 0° C. and trifluoroacetic acid (0.8 ml) was slowly added dropwise. The resulting mixture was stirred at 0° C. for thirty minutes, followed by stirring at ambient temperature for thirty minutes. 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 intermediate was further purified by liquid chromatography.

Workup

stirringby stirring at ambient temperature for thirty minutes
customThe reaction mixture was partitioned between 1 M potassium carbonate and methylene chloride
extractionThe aqueous fraction was back extracted with methylene chloride
dry with materialdried over sodium sulfate
customThe solvents were removed in vacuo
customThe desired title intermediate was further purified by liquid chromatography

Sources & evidence

ORD record: ord-9514d72b810041cba97c15cfe54fc84a
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06245761B1

Reaction notes

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