Reacción #1509593

ord-6c79d15196694818ba830d22d9f3b43e

Ecuación de reacción

CCOC(=O)c1cc(N)cc(-c2nnnn2C)c1
3-Amino-5-(1-methyl-1H-tetrazol-5-yl)-benzoic acid ethyl ester
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
Cn1nnnc1-c1cc(N)cc(CO)c1
title compound
Rendimiento 33.7%
Cn1nnnc1-c1cc(N)cc(CO)c1
[3-Amino-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-methanol
Rendimiento 33.7%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONThe reaction mixture was poured onto ice-water
  2. 2
    Extracciónextracted into EtOAc
  3. 3
    OtroThe organic layer was separated
  4. 4
    Otrodried
  5. 5
    Concentraciónconcentrated in vacuum

Procedimiento

To a solution of 3-Amino-5-(1-methyl-1H-tetrazol-5-yl)-benzoic acid ethyl ester (250 mg) in THF (5 ml) at 0° C. was added pre-cooled 1M LiAlH4 solution in THF (2 ml) dropwise. This was stirred for 3 h. The reaction mixture was poured onto ice-water and extracted into EtOAc. The organic layer was separated, dried and concentrated in vacuum. Flash chromatography (100:0 to 95:5 gradient DCM:MeOH) afforded the title compound (70 mg).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: USRE045323E1uspto-grants-2015_01