2-(3-bromophenyl)-2-methylbutan-1-amine

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

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

Procedure: A solution of 2-(3-bromophenyl)-2-methylbutanenitrile (1678.5 mg, 7.049 mmol) in dry THF (28 mL) was cooled in an ice-bath. AlH3:(Me)2EtN complex, 0.5M in PhMe (28.20 mL of 0.5 M, 14.10 mmol) was added slowly dropwise and the resultant solution stirred at 0° C. for 30 mins. The mixture was allowed to warm to RT and stirred for 4.5 hours. The reaction was carefully quenched by dropwise addition of 1:1 THF:water (˜30 mL). The resulting suspension was stirred vigorously and filtered through a pad of celite. The collected solid was partitioned between EtOAc and brine and the aqueous layer further extracted with EtOAc (3×50 mL) and the combined organics dried over Na2SO4, filtered and concentrated under reduced pressure to give a light brown oil. The residue was purified on silica gel by flash column chromatography (5% MeOH in DCM, loaded in DCM, ˜200 mL silica) to give the product as a yellow oil (1137.8 mg, 67% Yield). The reaction was carefully quenched by dropwise addition of 1:1 THF The resulting suspension was stirred vigorously filtered through a pad of celite The collected solid was partitioned between EtOAc and brine the aqueous layer further extracted with EtOAc (3×50 mL) the combined organics dried over Na2SO4 filtered concentrated under reduced pressure to give a light brown oil The residue was purified on silica gel by flash column chromatography (5% MeOH in DCM, loaded in DCM, ˜200 mL silica)

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

Procedure: A solution of 2-(3-bromophenyl)-2-methylbutanenitrile (1678.5 mg, 7.049 mmol) in dry THF (28 mL) was cooled in an ice-bath. AlH3:(Me)2EtN complex, 0.5M in PhMe (28.20 mL of 0.5 M, 14.10 mmol) was added slowly dropwise and the resultant solution stirred at 0° C. for 30 mins. The mixture was allowed to warm to RT and stirred for 4.5 hours. The reaction was carefully quenched by dropwise addition of 1:1 THF:water (˜30 mL). The resulting suspension was stirred vigorously and filtered through a pad of celite. The collected solid was partitioned between EtOAc and brine and the aqueous layer further extracted with EtOAc (3×50 mL) and the combined organics dried over Na2SO4, filtered and concentrated under reduced pressure to give a light brown oil. The residue was purified on silica gel by flash column chromatography (5% MeOH in DCM, loaded in DCM, ˜200 mL silica) to give the product as a yellow oil (1137.8 mg, 67% Yield). The reaction was carefully quenched by dropwise addition of 1:1 THF The resulting suspension was stirred vigorously filtered through a pad of celite The collected solid was partitioned between EtOAc and brine the aqueous layer further extracted with EtOAc (3×50 mL) the combined organics dried over Na2SO4 filtered concentrated under reduced pressure to give a light brown oil The residue was purified on silica gel by flash column chromatography (5% MeOH in DCM, loaded in DCM, ˜200 mL silica)

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

Procedure: A solution of 2-(3-bromophenyl)-2-methylbutanenitrile (1678.5 mg, 7.049 mmol) in dry THF (28 mL) was cooled in an ice-bath. AlH3:(Me)2EtN complex, 0.5M in PhMe (28.20 mL of 0.5 M, 14.10 mmol) was added slowly dropwise and the resultant solution stirred at 0° C. for 30 mins. The mixture was allowed to warm to RT and stirred for 4.5 hours. The reaction was carefully quenched by dropwise addition of 1:1 THF:water (˜30 mL). The resulting suspension was stirred vigorously and filtered through a pad of celite. The collected solid was partitioned between EtOAc and brine and the aqueous layer further extracted with EtOAc (3×50 mL) and the combined organics dried over Na2SO4, filtered and concentrated under reduced pressure to give a light brown oil. The residue was purified on silica gel by flash column chromatography (5% MeOH in DCM, loaded in DCM, ˜200 mL silica) to give the product as a yellow oil (1137.8 mg, 67% Yield). The reaction was carefully quenched by dropwise addition of 1:1 THF The resulting suspension was stirred vigorously filtered through a pad of celite The collected solid was partitioned between EtOAc and brine the aqueous layer further extracted with EtOAc (3×50 mL) the combined organics dried over Na2SO4 filtered concentrated under reduced pressure to give a light brown oil The residue was purified on silica gel by flash column chromatography (5% MeOH in DCM, loaded in DCM, ˜200 mL silica)

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

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

Procedure: A solution of 2-(3-bromophenyl)-2-methylbutanenitrile (1678.5 mg, 7.049 mmol) in dry THF (28 mL) was cooled in an ice-bath. AlH3:(Me)2EtN complex, 0.5M in PhMe (28.20 mL of 0.5 M, 14.10 mmol) was added slowly dropwise and the resultant solution stirred at 0° C. for 30 mins. The mixture was allowed to warm to RT and stirred for 4.5 hours. The reaction was carefully quenched by dropwise addition of 1:1 THF:water (˜30 mL). The resulting suspension was stirred vigorously and filtered through a pad of celite. The collected solid was partitioned between EtOAc and brine and the aqueous layer further extracted with EtOAc (3×50 mL) and the combined organics dried over Na2SO4, filtered and concentrated under reduced pressure to give a light brown oil. The residue was purified on silica gel by flash column chromatography (5% MeOH in DCM, loaded in DCM, ˜200 mL silica) to give the product as a yellow oil (1137.8 mg, 67% Yield). The reaction was carefully quenched by dropwise addition of 1:1 THF The resulting suspension was stirred vigorously filtered through a pad of celite The collected solid was partitioned between EtOAc and brine the aqueous layer further extracted with EtOAc (3×50 mL) the combined organics dried over Na2SO4 filtered concentrated under reduced pressure to give a light brown oil The residue was purified on silica gel by flash column chromatography (5% MeOH in DCM, loaded in DCM, ˜200 mL silica)

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

Procedure: A solution of 2-(3-bromophenyl)-2-methylbutanenitrile (1678.5 mg, 7.049 mmol) in dry THF (28 mL) was cooled in an ice-bath. AlH3:(Me)2EtN complex, 0.5M in PhMe (28.20 mL of 0.5 M, 14.10 mmol) was added slowly dropwise and the resultant solution stirred at 0° C. for 30 mins. The mixture was allowed to warm to RT and stirred for 4.5 hours. The reaction was carefully quenched by dropwise addition of 1:1 THF:water (˜30 mL). The resulting suspension was stirred vigorously and filtered through a pad of celite. The collected solid was partitioned between EtOAc and brine and the aqueous layer further extracted with EtOAc (3×50 mL) and the combined organics dried over Na2SO4, filtered and concentrated under reduced pressure to give a light brown oil. The residue was purified on silica gel by flash column chromatography (5% MeOH in DCM, loaded in DCM, ˜200 mL silica) to give the product as a yellow oil (1137.8 mg, 67% Yield). The reaction was carefully quenched by dropwise addition of 1:1 THF The resulting suspension was stirred vigorously filtered through a pad of celite The collected solid was partitioned between EtOAc and brine the aqueous layer further extracted with EtOAc (3×50 mL) the combined organics dried over Na2SO4 filtered concentrated under reduced pressure to give a light brown oil The residue was purified on silica gel by flash column chromatography (5% MeOH in DCM, loaded in DCM, ˜200 mL silica)