Reacción #595410

Ecuación de reacción

title compound

Ethyl 5-(2-Hydroxy-3-(3-methoxyphenylamino)propyl)-8-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

LAH

MeOH

→

desired product

Rendimiento 5.0%

1-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-3-(3-methoxyphenylamino)propan-2-ol

Rendimiento 5.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto quench the remaining LAH
2. 2
   workup.WAITafter 45 min
3. 3
   Otrothe mixture was partitioned between EtOAc/H2O
4. 4
   OtroThe organic layer was separated
5. 5
   Extracciónthe aqueous layer was extracted with EtOAc (3×)
6. 6
   Lavadothe combined organic layers were washed with satd
7. 7
   Secadoaq. NaCl, dried over Na2SO4
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated
10. 10
    OtroThe crude residue was purified by column chromatography (SiO2, 0-20% MeOH/Acetone+1% Et3N)

Procedimiento

Following a literature procedure (Zoidis et al., Bioorg. Med. Chem. 2009, 17, 1534-1541), the title compound of Example 18 (0.015 g, 0.034 mmol) was dissolved in anhydrous THF (0.34 mL) and cooled to 0° C. A solution of LAH (0.10 mL, 1.0 M in THF) was added dropwise, and the reaction was stirred for 2 h at 0° C. MeOH was added to quench the remaining LAH and after 45 min, the mixture was partitioned between EtOAc/H2O. The organic layer was separated and the aqueous layer was extracted with EtOAc (3×), and the combined organic layers were washed with satd. aq. NaCl, dried over Na2SO4, filtered, and concentrated. The crude residue was purified by column chromatography (SiO2, 0-20% MeOH/Acetone+1% Et3N), followed by PTLC (10% MeOH/Acetone+1% Et3N) to afford the desired product (0.6 mg, 5%).

Fuente