3-methylpentan-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: Formic acid (65 mL, 17.2 mmol) was added dropwise to neat chlorosulfonyl isocyanate (1.5 mL, 17.2 mmol) at 0° C. with rapid stirring. Vigorous gas evolution was observed during the addition process. The resulting viscous suspension was stirred for 5 min at 0° C. during which time the mixture solidified. Dichloromethane (9 mL) was added and the solution was stirred for 1 h at 0° C. then 8 h at 25° C. The reaction mixture was cooled to 0° C. and a solution of 3-methylpentan-1-ol (11.5 mmol) and pyridine (1.4 mL, 17.2 mmol) in 8 mL of dichloromethane was added dropwise. The contents were warmed to 25° C. and stirred for 3 h. The reaction mixture was treated with EtOAc (80 mL) and water (50 mL), and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organic phase was washed with brine, dried over MgSO4, filtered and then concentrated. The crude product was purified by multiple flash chromatographies (7% ethyl acetate/dichloromethane) to give 3-methylpentyl sulfamate. the solution was stirred for 1 h at 0° C. 8 h at 25° C The reaction mixture was cooled to 0° C. The contents were warmed to 25° C. stirred for 3 h the aqueous layer was extracted with EtOAc (2×20 mL) The combined organic phase was washed with brine dried over MgSO4 filtered concentrated The crude product was purified by multiple flash chromatographies (7% ethyl acetate/dichloromethane)

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

Procedure: 3-(4-Methylhexyl)pyridine was prepared in a similar manner to that described above with regard to 3-hexylpyridine but using 3-methyl-1-pentylbromide [prepared by adding over 1 h, at -30° C. and under N2, 22.5 g of PBr3 (0.083 mol; 7.8 ml) to a mixture of 21.6 g (0.212 mol) of 3-methyl-1-pentanol, 3.95 g of anhydrous pyridine and 88.4 ml of anhydrous sulfuric ether; the mixture was allowed to react for 1 h at -30° C. and then for 1 night at room temperature; the reaction product was extracted and washed in the usual manner and purified on a Vigreux column to provide 20.8 g of pure product]. prepared by adding over 1 h, at -30° C. and under N2 to react for 1 h at -30° C. for 1 night at room temperature the reaction product was extracted washed in the usual manner purified on a Vigreux column

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

Procedure: 3-(4-Methylhexyl)pyridine was prepared in a similar manner to that described above with regard to 3-hexylpyridine but using 3-methyl-1-pentylbromide [prepared by adding over 1 h, at -30° C. and under N2, 22.5 g of PBr3 (0.083 mol; 7.8 ml) to a mixture of 21.6 g (0.212 mol) of 3-methyl-1-pentanol, 3.95 g of anhydrous pyridine and 88.4 ml of anhydrous sulfuric ether; the mixture was allowed to react for 1 h at -30° C. and then for 1 night at room temperature; the reaction product was extracted and washed in the usual manner and purified on a Vigreux column to provide 20.8 g of pure product]. prepared by adding over 1 h, at -30° C. and under N2 to react for 1 h at -30° C. for 1 night at room temperature the reaction product was extracted washed in the usual manner purified on a Vigreux column

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

Procedure: To a solution of 1.67 gms of 3-methyl pentanol in 40 ml of dimethylformamide, 0.62 gms of sodium hydride are added; and the reaction mixture is stirred at room temperature for 1 hour. To this solution is added 4.0 gms of the protected bromo-alcohol and the reaction mixture is stirred at room temperature for 17 hours. The reaction mixture is then partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum to give a yellow liquid. To a solution of 4.0 gms of this liquid in 240 ml of methanol is added 0.40 gms of p-toluenesulfonic acid and the reaction is stirred at room temperature for 16 hours. The methanol is removed under reduced pressure, and the residue is partitioned between ethyl acetate and water. The organic layer is washed with aqueous NaHCO3 and brine, then dried over Na2SO4, filtered, and concentrated under vacuum to give 8-(3-methylpentyloxy)octanol. the reaction mixture is stirred at room temperature for 17 hours The reaction mixture is then partitioned between ethyl acetate and water The organic layer is washed with brine dried over Na2SO4 filtered concentrated under vacuum to give a yellow liquid the reaction is stirred at room temperature for 16 hours The methanol is removed under reduced pressure the residue is partitioned between ethyl acetate and water The organic layer is washed with aqueous NaHCO3 and brine dried over Na2SO4 filtered concentrated under vacuum

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

Procedure: To a solution of 1.67 gms of 3-methyl pentanol in 40 ml of dimethylformamide, 0.62 gms of sodium hydride are added; and the reaction mixture is stirred at room temperature for 1 hour. To this solution is added 4.0 gms of the protected bromo-alcohol and the reaction mixture is stirred at room temperature for 17 hours. The reaction mixture is then partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum to give a yellow liquid. To a solution of 4.0 gms of this liquid in 240 ml of methanol is added 0.40 gms of p-toluenesulfonic acid and the reaction is stirred at room temperature for 16 hours. The methanol is removed under reduced pressure, and the residue is partitioned between ethyl acetate and water. The organic layer is washed with aqueous NaHCO3 and brine, then dried over Na2SO4, filtered, and concentrated under vacuum to give 8-(3-methylpentyloxy)octanol. the reaction mixture is stirred at room temperature for 17 hours The reaction mixture is then partitioned between ethyl acetate and water The organic layer is washed with brine dried over Na2SO4 filtered concentrated under vacuum to give a yellow liquid the reaction is stirred at room temperature for 16 hours The methanol is removed under reduced pressure the residue is partitioned between ethyl acetate and water The organic layer is washed with aqueous NaHCO3 and brine dried over Na2SO4 filtered concentrated under vacuum

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

Procedure: The title compound was prepared by following the general procedure of Example 43 for mesylation as a colorless oil (384 mg, 67%) from 3-methyl-1-pentanol (300 mg, 2.90 mmol) and methanesulfonyl chloride (500 mg, 4.40 mmol). 1H NMR (CDCl3, 300 MHz) δ0.86-0.95 (m, 6H), 1.15-1.25 (m, 1H), 1.33-1.42 (m, 1H), 1.51-1.60 (m, 2H), 1.76-1.84 (m, 1H), 3.00 (s, 3H), 4.23-4.31 (m, 2H) ppm.

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

Procedure: To a solution of 1.67 gms of 3-methyl pentanol in 40 ml of dimethylformamide, 0.62 gms of sodium hydride are added; and the reaction mixture is stirred at room temperature for 1 hour. To this solution is added 4.0 gms of the protected bromo-alcohol and the reaction mixture is stirred at room temperature for 17 hours. The reaction mixture is then partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum to give a yellow liquid. To a solution of 4.0 gms of this liquid in 240 ml of methanol is added 0.40 gms of p-toluenesulfonic acid and the reaction is stirred at room temperature for 16 hours. The methanol is removed under reduced pressure, and the residue is partitioned between ethyl acetate and water. The organic layer is washed with aqueous NaHCO3 and brine, then dried over Na2SO4, filtered, and concentrated under vacuum to give 8-(3-methylpentyloxy)octanol. the reaction mixture is stirred at room temperature for 17 hours The reaction mixture is then partitioned between ethyl acetate and water The organic layer is washed with brine dried over Na2SO4 filtered concentrated under vacuum to give a yellow liquid the reaction is stirred at room temperature for 16 hours The methanol is removed under reduced pressure the residue is partitioned between ethyl acetate and water The organic layer is washed with aqueous NaHCO3 and brine dried over Na2SO4 filtered concentrated under vacuum

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

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

Procedure: The title compound was prepared by following the general procedure of Example 43 for mesylation as a colorless oil (384 mg, 67%) from 3-methyl-1-pentanol (300 mg, 2.90 mmol) and methanesulfonyl chloride (500 mg, 4.40 mmol). 1H NMR (CDCl3, 300 MHz) δ0.86-0.95 (m, 6H), 1.15-1.25 (m, 1H), 1.33-1.42 (m, 1H), 1.51-1.60 (m, 2H), 1.76-1.84 (m, 1H), 3.00 (s, 3H), 4.23-4.31 (m, 2H) ppm.

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

Procedure: To a solution of 1.67 gms of 3-methyl pentanol in 40 ml of dimethylformamide, 0.62 gms of sodium hydride are added; and the reaction mixture is stirred at room temperature for 1 hour. To this solution is added 4.0 gms of the protected bromo-alcohol and the reaction mixture is stirred at room temperature for 17 hours. The reaction mixture is then partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum to give a yellow liquid. To a solution of 4.0 gms of this liquid in 240 ml of methanol is added 0.40 gms of p-toluenesulfonic acid and the reaction is stirred at room temperature for 16 hours. The methanol is removed under reduced pressure, and the residue is partitioned between ethyl acetate and water. The organic layer is washed with aqueous NaHCO3 and brine, then dried over Na2SO4, filtered, and concentrated under vacuum to give 8-(3-methylpentyloxy)octanol. the reaction mixture is stirred at room temperature for 17 hours The reaction mixture is then partitioned between ethyl acetate and water The organic layer is washed with brine dried over Na2SO4 filtered concentrated under vacuum to give a yellow liquid the reaction is stirred at room temperature for 16 hours The methanol is removed under reduced pressure the residue is partitioned between ethyl acetate and water The organic layer is washed with aqueous NaHCO3 and brine dried over Na2SO4 filtered concentrated under vacuum