dodec-11-en-1-ol

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

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 11-dodecen-1-ol (5.5 g, 29.9 mmol) in dichloromethane (70 mL) at 0° C. was added methanesulfonyl chloride (3.55 g, 2.40 mL, 31.0 mmol) followed by triethylamine (4.38 g, 46.0 mmol). After stirring for 10 minutes at 0° C., the reaction was allowed to warm to 25° C. and stirred for 2 hours. The reaction was poured into water (60 mL), separated and washed with dichloromethane (50 mL). The organic portions were combined, dried using magnesium sulfate, and evaporated to yield 12-methanesulfonyl-1-dodecene as a yellow oil which was then used without further purification. to warm to 25° C. stirred for 2 hours separated washed with dichloromethane (50 mL) dried evaporated

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

Procedure: This example illustrates a synthesis of 1-(11,12-Oxidododecyl)-3,7-dimethylxanthine (inventive compound no. 2518). To a suspension of magnesium (6.4 g, 265 mmol) and a crystal of iodine in tetrahydrofuran (40 mL) was added 10-undecenyl bromide (12.25 g, 53.0 mmol, available from MTM) in tetrahydrofuran (30 mL) over 30 minutes and the reaction stirred for a further 30 minutes after the addition was complete. The solution was added via a canula over 5 minutes to a suspension of paraformaldehyde (1.80 g, 60.0 mmol) in tetrahydrofuran (40 mL) and stirred at 25° C. for 16 hours. Saturated ammonium chloride (80 mL) is added and extracted with diethyl ether (2×100 mL). The combined organic extracts are dried using magnesium sulfate and evaporated to give a residue which is distilled at 2 mm Hg to yield 6.53 g (67% yield, b.p. 105°-107° C.) of 11-dodecenyl alcohol as a clear liquid. after the addition stirred at 25° C. for 16 hours extracted with diethyl ether (2×100 mL) The combined organic extracts are dried evaporated to give a residue which is distilled at 2 mm Hg

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of l1 -dodecen-1-ol (5.5 g, 29.9 mmol) in dichloromethane (70 ml) at 0° C. was added methanesulfonyl chloride (3.55 g, 2.40 ml, 31.0 mmol) followed by triethylamine (4.38 g, 46.0 mmol). After stirring for 10 minutes at 0° C., the reaction was allowed to warm to 25° C. and stirred for 2 hours. The reaction was poured into water (60 ml), separated and washed with dichloromethane (50 ml). The organic portions were combined, dried with magnesium sulfate, and evaporated, yielding 12-methanesulfonyl-1-dodecene as a yellow oil which was used without further purification. To a suspension of sodium theobromine (6.00 g, 30.0 mmol) in dimethylsulfoxide (60 mL) was added 12-methanesulfonyl-1-dodecene. The resulting reaction mixture was stirred for 16 hours at 60° C. The mixture was then poured into water (120 ml) and extracted with diethyl ether (2×100 ml). The organic portions were combined, dried with magnesium sulfate. The evaporated solvent left a cream-colored solid. Recrystallization from ethyl acetate/hexane (1:1) yielded 6.97 g of a white solid, 1-(l1-dodecenyl)-3,7-dimethylxanthine as a white solid (67% yield). to warm to 25° C. stirred for 2 hours separated washed with dichloromethane (50 ml) dried with magnesium sulfate evaporated

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

Procedure: This example illustrates a synthetic protocol for inventive compound no. 2525 (see above for chemical name and formula). To a suspension of magnesium (6.4 g, 265 mmol) and a crystal of iodine in tetrahydrofuran (40 ml) was added 10-undecenyl bromide (Syn. Comm. 1984, 14, 591-597: 12.25 g, 53.0 mmol) in tetrahydrofuran (30 ml) over 30 minutes and the reaction was stirred for a further 30 minutes after the addition was complete. The solution was added via a canula over 5 minutes to a suspension of paraformaldehyde (1.80 g, 60.0 mmol) in tetrahydrofuran (40 ml) and stirred at 25° C. for 16 hours. Saturated ammonium chloride (80 ml) was added and extracted with diethyl ether (2×100 ml). The combined organic extracts were dried (magnesium sulfate) and evaporated to give a residue which was distilled at 2 mm Hg, yielding a clear liquid alcohol, 11-dodecen-1-ol (6.53 g, 67 %, b.p. 105°-107° C.). after the addition stirred at 25° C. for 16 hours extracted with diethyl ether (2×100 ml) The combined organic extracts were dried (magnesium sulfate) evaporated to give a residue which was distilled at 2 mm Hg

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

Procedure: This example illustrates a synthetic protocol for inventive compound no. 2525 (see above for chemical name and formula). To a suspension of magnesium (6.4 g, 265 mmol) and a crystal of iodine in tetrahydrofuran (40 ml) was added 10-undecenyl bromide (Syn. Comm. 1984, 14, 591-597: 12.25 g, 53.0 mmol) in tetrahydrofuran (30 ml) over 30 minutes and the reaction was stirred for a further 30 minutes after the addition was complete. The solution was added via a canula over 5 minutes to a suspension of paraformaldehyde (1.80 g, 60.0 mmol) in tetrahydrofuran (40 ml) and stirred at 25° C. for 16 hours. Saturated ammonium chloride (80 ml) was added and extracted with diethyl ether (2×100 ml). The combined organic extracts were dried (magnesium sulfate) and evaporated to give a residue which was distilled at 2 mm Hg, yielding a clear liquid alcohol, 11-dodecen-1-ol (6.53 g, 67 %, b.p. 105°-107° C.). after the addition stirred at 25° C. for 16 hours extracted with diethyl ether (2×100 ml) The combined organic extracts were dried (magnesium sulfate) evaporated to give a residue which was distilled at 2 mm Hg

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 11-dodecen-1-ol (5.5 g, 29.9 mmol) in dichloromethane (70 ml) at 0° C. was added methanesulfonyl chloride (3.55 g, 2.40 ml, 31.0 mmol) followed by triethylamine (4.38 g, 46.0 mmol). After stirring for 10 min at 0° C., the reaction was allowed to warm to 25° C. and stirred for 2 hr. The reaction was poured into water (60 ml), separated and washed with dichloromethane (50 ml). The organic portions were combined, dried (magnesium sulfate), and evaporated to give the 12-methanesulfonyl-1-dodecene as a yellow oil which was used without further purification. to warm to 25° C. stirred for 2 hr separated washed with dichloromethane (50 ml) dried (magnesium sulfate) evaporated

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

Procedure: This example illustrates the synthesis of 1-(11-Dodecenyl)-3,7-dimethylxanthine (CT2516). To a suspension of magnesium (6.4 g, 265 mmol) and a crystal of iodine in tetrahydrofuran (40 ml) was added 10-undecenyl bromide (12.25 g, 53.0 mmol) in tetrahydrofuran (30 ml) over 30 min and the reaction stirred for a further 30 min after the addition was complete. The solution was added via a canula over 5 min to a suspension of paraformaldehyde (1.80 g, 60.0 mmol) in tetrahydrofuran (40 ml) and stirred at 25° C. for 16 hr. Saturated ammonium chloride (80 ml) was added and extracted with diethyl ether (2×100 ml). The combined organic extracts were dried (magnesium sulfate) and evaporated to give a residue which was distilled at 2 mm Hg to afford 11-dodecenyl alcohol as a clear liquid (6.53 g, 67%, b.p. 105°-107° C.). after the addition stirred at 25° C. for 16 hr extracted with diethyl ether (2×100 ml) The combined organic extracts were dried (magnesium sulfate) evaporated to give a residue which was distilled at 2 mm Hg

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

Procedure: This example illustrates the synthesis of 1-(11-Dodecenyl)-3,7-dimethylxanthine (CT2516). To a suspension of magnesium (6.4 g, 265 mmol) and a crystal of iodine in tetrahydrofuran (40 ml) was added 10-undecenyl bromide (12.25 g, 53.0 mmol) in tetrahydrofuran (30 ml) over 30 min and the reaction stirred for a further 30 min after the addition was complete. The solution was added via a canula over 5 min to a suspension of paraformaldehyde (1.80 g, 60.0 mmol) in tetrahydrofuran (40 ml) and stirred at 25° C. for 16 hr. Saturated ammonium chloride (80 ml) was added and extracted with diethyl ether (2×100 ml). The combined organic extracts were dried (magnesium sulfate) and evaporated to give a residue which was distilled at 2 mm Hg to afford 11-dodecenyl alcohol as a clear liquid (6.53 g, 67%, b.p. 105°-107° C.). after the addition stirred at 25° C. for 16 hr extracted with diethyl ether (2×100 ml) The combined organic extracts were dried (magnesium sulfate) evaporated to give a residue which was distilled at 2 mm Hg

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 11-dodecen-1-ol (5.5 g, 29.9 mmol) in dichloromethane (70 mL) at 0° C. was added methanesulfonyl chloride (3.55 g, 2.40 mL, 31.0 mmol) followed by triethylamine (4.38 g, 46.0 mmol). After stirring for 10 minutes at 0° C., the reaction was allowed to warm to 25° C. and stirred for 2 hours. The reaction was poured into water (60 mL), separated and washed with dichloromethane (50 mL). The organic portions were combined, dried using magnesium sulfate, and evaporated to yield 12-methanesulfonyl-1-dodecene as a yellow oil which was then used without further purification. to warm to 25° C. stirred for 2 hours separated washed with dichloromethane (50 mL) dried evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 11-dodecen-1-ol (5.5 g, 29.9 mmol) in dichloromethane (70 mL) at 0° C. was added methanesulfonyl chloride (3.55 g, 2.40 mL, 31.0 mmol) followed by triethylamine (4.38 g, 46.0 mmol). After stirring for 10 minutes at 0° C., the reaction was allowed to warm to 25° C. and stirred for 2 hours. The reaction was poured into water (60 mL), separated and washed with dichloromethane (50 mL). The organic portions were combined, dried using magnesium sulfate, and evaporated to yield 12-methanesulfonyl-1-dodecene as a yellow oil which was then used without further purification. to warm to 25° C. stirred for 2 hours separated washed with dichloromethane (50 mL) dried evaporated