ethyl 8-bromooctanoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The product is produced as described in example 1 from 3.0 g. of NaH (80% suspension in mineral oil), 13.5 g. of benzoxazolin-2-one, 200 cc. of DMF, 23.7 g. of 8-bromocaprylic acid ethyl ester and 3.0 g. of NaJ. Eluant in chromatographic purification: hexane/ethyl acetate. The product is produced Eluant in chromatographic purification

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 26.4 g (0.1 mole) of ethyl-8-bromooctanoate (95%, Pfaltz and Bauer) and 19.6 g (0.1 mole) of potassium phthalimide (98%, Aldrich) in 250 mL of dimethylformamide was stirred and heated at reflux for 4 hr. The solvent was evaporated under reduced pressure and the viscous residue was partitioned between ethyl ether and water (400 mL each). The aqueous layer was further extracted with two 200 mL of ethyl ether. The combined ether extracts were washed with 200 mL of water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the viscous, oily residue was triturated with ethyl ether-petroleum ether (30°-60° C.) and the resulting solid was collected by filtration. The filtrate was evaporated under reduced pressure to give 25.2 g (79%) of crude title compound as a viscous oil. A 2.0 g sample of this oil was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500A; PrepPak® 500 silica; ethyl acetate-hexanes, 1:20; flow rate: 200 mL/min.). Fractions containing title compound were combined and the solvents were evaporated under reduced pressure to give 1.9 g (95% recovery) of clear liquid. heated at reflux for 4 hr The solvent was evaporated under reduced pressure the viscous residue was partitioned between ethyl ether and water (400 mL each) The aqueous layer was further extracted with two 200 mL of ethyl ether The combined ether extracts were washed with 200 mL of water dried over magnesium sulfate The solvent was evaporated under reduced pressure the viscous, oily residue was triturated with ethyl ether-petroleum ether (30°-60° C.) the resulting solid was collected by filtration The filtrate was evaporated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: This compound was prepared according to the procedure used in Example 7. A mixture of 4.6 g (0.015 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 3.8 g (0.015 mole) of ethyl 8-bromooctanoate, 6.4 g (0.061 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 50 ml of N,N-dimethylformamide gave 6.7 g of a dark oil. The oil was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500A; PrepPAK® 500/silica; ethyl acetate-hexane 2:1; flow rate 150 ml/min). The fractions containing the desired product were combined and concentrated under reduced pressure to yield 4.3 g (72%) of the title compound as a viscous, yellow oil. This compound was prepared