1-methoxybutan-2-ol

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

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

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

Procedure: To a solution of 1-methoxybutan-2-ol (1.10 mL) in pyridine (5 mL) was added dropwise a solution of 4-methylbenzenesulfonyl chloride (2.75 g) in pyridine (15 mL) over 30 min or more at 0° C. The reaction mixture was stirred overnight at room temperature, and poured into ice-water. The reaction mixture was stirred at 0° C. for 1 hr, and the precipitate was collected by filtration, and washed with cold water. The obtained solid was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.23 g). The reaction mixture was stirred at 0° C. for 1 hr the precipitate was collected by filtration washed with cold water The obtained solid was purified by silica gel column chromatography (hexane/ethyl acetate)

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

Procedure: To a solution of 1-methoxybutan-2-ol (1.10 mL) in pyridine (5 mL) was added dropwise a solution of 4-methylbenzenesulfonyl chloride (2.75 g) in pyridine (15 mL) over 30 min or more at 0° C. The reaction mixture was stirred overnight at room temperature, and poured into ice-water. The reaction mixture was stirred at 0° C. for 1 hr, and the precipitate was collected by filtration, and washed with cold water. The obtained solid was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.23 g). The reaction mixture was stirred at 0° C. for 1 hr the precipitate was collected by filtration washed with cold water The obtained solid was purified by silica gel column chromatography (hexane/ethyl acetate)

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

Procedure: The title compound was synthesized in analogy to the procedure described for the preparation of Example 43, using 5-bromo-6-chloro-nicotinic acid methyl ester, 4-chlorophenyl-boronic acid (commercially available), rac-1-methoxy-2-butanol (commercially available), and (1R,2R)-2-amino-cyclohexanol (commercially available) as starting materials. MS (ISP): 433.3, 435.3 (M+H+). described for the preparation of Example 43

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1-methoxy-2-butanol (52.08 g, 57.23 mL, 0.5 mol) and Et3N (108.2 mL, 0.75 mol, 1.5 equiv) in CH2Cl2 (500 mL) was treated dropwise with methanesulfonyl chloride (68.73 g, 46.44 mL, 0.6 mol, 1.2 equiv) at 0° C. under N2. The reaction mixture was warmed to 25° C. and stirred at 25° C. for an additional 4 h before being quenched with H2O (300 mL). The two layers were separated, and the aqueuos was extracted with CH2Cl2 (3×100 mL). The combined CH2Cl2 extracts were washed with H2O (2×200 mL) and saturated aqueuos NaCl (200 mL), dried (MgSO4), and concentrated in vacuo. The residue was dried enough in vacuo to afforded the desired mesylate 1 (85-90.0 g, 91 g theoretical, 93-98%) as a pale-yellow oil, which was pure enough and directly used in the next reaction without further purification. before being quenched with H2O (300 mL) The two layers were separated the aqueuos was extracted with CH2Cl2 (3×100 mL) The combined CH2Cl2 extracts were washed with H2O (2×200 mL) and saturated aqueuos NaCl (200 mL) dried (MgSO4) concentrated in vacuo The residue was dried enough in vacuo

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

Procedure: The title compound was synthesized in analogy to the procedure described for the preparation of Example 43, using 5-bromo-6-chloro-nicotinic acid methyl ester, 4-chlorophenyl-boronic acid (commercially available), rac-1-methoxy-2-butanol (commercially available), and (1R,2R)-2-amino-cyclohexanol (commercially available) as starting materials. MS (ISP): 433.3, 435.3 (M+H+). described for the preparation of Example 43