Diisobutylaluminum hydride → ((1r)-1-Phenylethyl){[3-(4-methoxyphenyl)-4-methylphenyl]methyl}amine

To a solution of N-((1R)-1-phenylethyl)[3-(4-methoxyphenyl)-4-methylphenyl]carboxamide (0.12 g, 0.34 mmol) in 10 mL of toluene was added DIBAL-H (1 mL, 1.5 mmol). The reaction was then heated to 100 C for 16 hours and cooled to RT. The reaction was quenched with 5 mL of 2N NaOH aq. soln. 100 mL of CH2Cl2 was used to extract the product. The organic phase was washed with 30 mL of brine, dried over Na2SO3 and concentrated in vacuo. The desired products were separated by silica gel column chromatography (30% to 60% EtOAc in hexane) provide ((1R)-1-phenylethyl){[3-(4-methoxyphenyl)-4-methylphenyl]methyl}amine and 4-(5-{[((1R)-1-phenylethyl)amino]methyl}-2-methylphenyl)phenol, which were treated with 1N HCl in Et2O separately to provide the HCl salts as white solids.

1. temperatureThe reaction was then heated to 100 C for 16 hours
2. customThe reaction was quenched with 5 mL of 2N NaOH aq. soln
3. extractionto extract the product
4. washThe organic phase was washed with 30 mL of brine
5. dry with materialdried over Na2SO3
6. concentrationconcentrated in vacuo
7. customThe desired products were separated by silica gel column chromatography (30% to 60% EtOAc in hexane)

ORD 기록

ord-5e8f89dde42b4528a0c5cdfe019d2fc5

출처 데이터셋

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07524873B2