2-(2-fluorophenyl)-2-methylpropan-1-ol

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

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

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

Procedure: Borane-methyl sulfide (2M in THF, 12.35 mL) was added dropwise to a solution of 2-(2-fluorophenyl)-2-methylpropanoic acid (example 90, step c) (1.5 g) in THF (30 mL). The reaction mixture was stirred at 20° C. for 8 hours. The mixture was quenched by careful addition of methanol until evolution of gas ceased. The solvents were removed under reduced pressure and the residue azeotroped with toluene. The crude product was purified by flash silica chromatography using 30% ethyl acetate in isohexane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 1.3 g. The mixture was quenched by careful addition of methanol until evolution of gas The solvents were removed under reduced pressure the residue azeotroped with toluene The crude product was purified by flash silica chromatography Pure fractions were evaporated to dryness

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: tert-Butyldimethylsilyl chloride (1.4 g) was added portionwise to a stirred solution of 2-(2-fluorophenyl)-2-methylpropan-1-ol (example 90, step d) (1.3 g) and imidazole (0.631 g) in DMF (7 mL) at 20° C. The reaction mixture was stirred for 3 hours at room temperature and then partitioned between ethyl acetate and brine. The organic layer was washed twice with brine, dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography, elution gradient 100% isohexane to 1% diethyl ether in isohexane. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 1.4 g. partitioned between ethyl acetate and brine The organic layer was washed twice with brine dried over sodium sulphate filtered the solvent evaporated under reduced pressure The crude product was purified by flash silica chromatography, elution gradient 100% isohexane to 1% diethyl ether in isohexane Pure fractions were evaporated to dryness

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

Procedure: Borane-methyl sulfide (2M in THF, 12.35 mL) was added dropwise to a solution of 2-(2-fluorophenyl)-2-methylpropanoic acid (example 90, step c) (1.5 g) in THF (30 mL). The reaction mixture was stirred at 20° C. for 8 hours. The mixture was quenched by careful addition of methanol until evolution of gas ceased. The solvents were removed under reduced pressure and the residue azeotroped with toluene. The crude product was purified by flash silica chromatography using 30% ethyl acetate in isohexane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 1.3 g. The mixture was quenched by careful addition of methanol until evolution of gas The solvents were removed under reduced pressure the residue azeotroped with toluene The crude product was purified by flash silica chromatography Pure fractions were evaporated to dryness

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

Procedure: Borane-methyl sulfide (2M in THF, 12.35 mL) was added dropwise to a solution of 2-(2-fluorophenyl)-2-methylpropanoic acid (example 90, step c) (1.5 g) in THF (30 mL). The reaction mixture was stirred at 20° C. for 8 hours. The mixture was quenched by careful addition of methanol until evolution of gas ceased. The solvents were removed under reduced pressure and the residue azeotroped with toluene. The crude product was purified by flash silica chromatography using 30% ethyl acetate in isohexane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 1.3 g. The mixture was quenched by careful addition of methanol until evolution of gas The solvents were removed under reduced pressure the residue azeotroped with toluene The crude product was purified by flash silica chromatography Pure fractions were evaporated to dryness

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