Boron tribromide → HCID 23141683, compound

HRID 32265Notes

Reaction equation

HRID 32265 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[O:21]C)[CH2:10][CH2:9]1)=O)(C)(C)C.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[F:20][C:18]1[CH:17]=[CH:16][C:15]([OH:21])=[C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 597693774-(5-Fluoro-2-methoxyphenyl)piperidine-1-carboxylic acid t-butyl ester

Product 1

HCID 23141683HCID 23141683, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(5-fluoro-2-methoxyphenyl)piperidine-1-carboxylic acid t-butyl ester (2.0 g, 6.46 mmol) produced in Example (106b) in dichloromethane (50 mL) was added boron tribromide (1M solution in tetrahydrofuran, 19.4 mL, 19.4 mmol), followed by stirring for 4 hours at an external temperature of 60° C. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure to give 840 mg of a crude product of the title compound as a yellow oil.

Workup

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-635e6deb405b49fea500aa45d81e5af9
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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