methyl 7-bromoheptanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 2-phenylethylamine (1.09 g, 9 mmol) and triethylamine (1.37 g, 13.5 mmol) in toluene (50 mL) was added methyl 7-bromoheptanoate (2.0 g, 9 mmol) and refluxed overnight. The reaction mixture was filtered and concentrated. Flash column chromatography over silica gel using 100% ethyl acetate yielded a yellow oil (0.62 g, 20%) NMR (250 MHz, CDCl3), 1.12-1.40 (4H, m), 1.40-1.72 (4H, m), 2.29 (2H, t), 2.63 (2H, t), 2.75-2.96 (4H, m), 2.96-3.1 (1H, br s), 3.66 (3H, s), 7.00-7.38 (5H, m). refluxed overnight The reaction mixture was filtered concentrated

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add sodium cyanide (12.5 g, 255 mmol) and tetra-n-butylammonium iodide (10 g, 27.0 mmol) portionwise to a solution of 7-bromoheptanoic acid methyl ester (25 g, 105 mmol) in DMSO (300 mL) at room temperature under nitrogen and heat the mixture at 50° C. for 4 hours. Cool the mixture and dilute with water (200 mL) and extract with diethyl ether (2×200 mL). Dry the combined organic extracts over sodium sulfate and remove the solvent under reduced pressure to provide 7-cyanoheptanoic acid ethyl ester (18.2 g, 94%). Cool the mixture extract with diethyl ether (2×200 mL) Dry the combined organic extracts over sodium sulfate remove the solvent under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Alternatively 6-(5-oxocyclopent-1-enyl)-4-hexenoic acid methyl ester, 7-(5-oxocyclopent-1-enyl)-5-heptenoic acid methyl ester and 8-(5-oxocyclopent-1-enyl)-6-octenoic acid methyl ester, as well as, 6-(5-oxocyclopent-1enyl)hexanoic acid methyl ester, 7-(5-oxocyclopent-1-enyl)heptanoic acid methyl ester, and 8-(5-oxocyclopent-1-enyl)octanoic methyl ester are prepared by following serially the procedures of Examples 13, 14 and 15, and using methyl 6-bromo-4-hexenoate, methyl 7-bromo-5-heptanoate, methyl 8-bromo-6-octenoate, methyl 6-bromohexanoate, methyl 7-bromoheptanoate, and methyl 8-bromooctanoate, respectively, as starting material instead of methyl 7-bromo-5-heptynoate.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 2-phenylethylamine (1.09 g, 9 mmol) and triethylamine (1.37 g, 13.5 mmol) in toluene (50 mL) was added methyl 7-bromoheptanoate (2.0 g, 9 mmol) and refluxed overnight. The reaction mixture was filtered and concentrated. Flash column chromatography over silica gel using 100% ethyl acetate yielded a yellow oil (0.62 g, 20%) NMR (250 MHz, CDCl3), 1.12-1.40 (4H, m), 1.40-1.72 (4H, m), 2.29 (2H, t), 2.63 (2H, t), 2.75-2.96 (4H, m), 2.96-3.1 (1H, br s), 3.66 (3H, s), 7.00-7.38 (5H, m). refluxed overnight The reaction mixture was filtered concentrated

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 2-phenylethylamine (1.09 g, 9 mmol) and triethylamine (1.37 g, 13.5 mmol) in toluene (50 mL) was added methyl 7-bromoheptanoate (2.0 g, 9 mmol) and refluxed overnight. The reaction mixture was filtered and concentrated. Flash column chromatography over silica gel using 100% ethyl acetate yielded a yellow oil (0.62 g, 20%) NMR (250 MHz, CDCl3), 1.12-1.40 (4H, m), 1.40-1.72 (4H, m), 2.29 (2H, t), 2.63 (2H, t), 2.75-2.96 (4H, m), 2.96-3.1 (1H, br s), 3.66 (3H, s), 7.00-7.38 (5H, m). refluxed overnight The reaction mixture was filtered concentrated

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 100 mg of 4-chloro-N-(1,2-diphenyl-1H-benzimidazol-5-yl)benzenesulfonamide was suspended in 0.5 ml of N,N-dimethylformamide, mixed with 8 mg of sodium hydride, and stirred for 30 minutes at 20° C. 70 mg of 7-bromoheptanoic acid methyl ester was added, it was allowed to stir for 15 hours, mixed with water, extracted three times with ethyl acetate, the extracts were dried on sodium sulfate, concentrated by evaporation in a vacuum, and the residue was chromatographed on silica gel. to stir for 15 hours extracted three times with ethyl acetate the extracts were dried on sodium sulfate concentrated by evaporation in a vacuum the residue was chromatographed on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 2-phenylethylamine (1.09 g, 9 mmol) and triethylamine (1.37 g, 13.5 mmol) in toluene (50 mL) was added methyl 7-bromoheptanoate (2.0 g, 9 mmol) and refluxed overnight. The reaction mixture was filtered and concentrated. Flash column chromatography over silica gel using 100% ethyl acetate yielded a yellow oil (0.62 g, 20%) NMR (250 MHz, CDCl3), 1.12-1.40 (4H, m) , 1.40-1.72 (4H, m), 2.29 (2H, t), 2.63 (2H, t), 2.75-2.96 (4H, m), 2.96-3.1 (1H, br s), 3.66 (3H, s), 7.00-7.38 (5H, m). refluxed overnight The reaction mixture was filtered concentrated

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add sodium cyanide (12.5 g, 255 mmol) and tetra-n-butylammonium iodide (10 g, 27.0 mmol) portionwise to a solution of 7-bromoheptanoic acid methyl ester (25 g, 105 mmol) in DMSO (300 mL) at room temperature under nitrogen and heat the mixture at 50° C. for 4 hours. Cool the mixture and dilute with water (200 mL) and extract with diethyl ether (2×200 mL). Dry the combined organic extracts over sodium sulfate and remove the solvent under reduced pressure to provide 7-cyanoheptanoic acid ethyl ester (18.2 g, 94%). Cool the mixture extract with diethyl ether (2×200 mL) Dry the combined organic extracts over sodium sulfate remove the solvent under reduced pressure

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add sodium cyanide (12.5 g, 255 mmol) and tetra-n-butylammonium iodide (10 g, 27.0 mmol) portionwise to a solution of 7-bromoheptanoic acid methyl ester (25 g, 105 mmol) in DMSO (300 mL) at room temperature under nitrogen and heat the mixture at 50° C. for 4 hours. Cool the mixture and dilute with water (200 mL) and extract with diethyl ether (2×200 mL). Dry the combined organic extracts over sodium sulfate and remove the solvent under reduced pressure to provide 7-cyanoheptanoic acid ethyl ester (18.2 g, 94%). Cool the mixture extract with diethyl ether (2×200 mL) Dry the combined organic extracts over sodium sulfate remove the solvent under reduced pressure

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 100 mg of 4-chloro-N-(1,2-diphenyl-1H-benzimidazol-5-yl)benzenesulfonamide was suspended in 0.5 ml of N,N-dimethylformamide, mixed with 8 mg of sodium hydride, and stirred for 30 minutes at 20° C. 70 mg of 7-bromoheptanoic acid methyl ester was added, it was allowed to stir for 15 hours, mixed with water, extracted three times with ethyl acetate, the extracts were dried on sodium sulfate, concentrated by evaporation in a vacuum, and the residue was chromatographed on silica gel. to stir for 15 hours extracted three times with ethyl acetate the extracts were dried on sodium sulfate concentrated by evaporation in a vacuum the residue was chromatographed on silica gel