반응 #73339

반응 방정식

imidazole

TBSCl

EtOAc

3-Amino-5-trifluoromethyl-benzoic acid

LiAlH4

NaF

→

title compound

3-(tert-Butyl-dimethyl-silanyloxymethyl)-5-trifluoromethyl-phenylamine

용매

H2O

DCM

THF

THF

반응 조건

후처리

1. 1
   온도The mixture is warmed
2. 2
   온도to reflux
3. 3
   workup.STIRRINGThe slurry is stirred for 10 minutes
4. 4
   온도to warm to rt
5. 5
   workup.STIRRINGstir an additional 40 min
6. 6
   여과The mixture is filtered
7. 7
   세척the solid is rinsed with EtOAc and MeOH
8. 8
   농축The filtrate is concentrated
9. 9
   workup.STIRRINGthe mixture is stirred at rt for 5 h
10. 10
    세척washed with saturated aqueous NaHCO3, brine
11. 11
    건조dried over Na2SO4
12. 12
    농축Concentration

실험 절차

To a solution of 3-Amino-5-trifluoromethyl-benzoic acid (2.0 g, 9.76 mmol) in THF (40 mL) at 0° C. is added LiAlH4 in THF (1 M, 39 mL). The mixture is warmed to reflux and stirred for 62 h. The mixture is then cooled to 0° C. and NaF (2.2 g) is added followed by H2O (3.8 mL). The slurry is stirred for 10 minutes and then allowed to warm to rt and stir an additional 40 min. The mixture is filtered and the solid is rinsed with EtOAc and MeOH. The filtrate is concentrated and the crude residue is mixed with imidazole (2.66 g, 39 mmol) and DCM (30 mL) at 0° C. TBSCl (3.5 g, 23.4 mmol) is added and the mixture is stirred at rt for 5 h. The reaction mixture is then diluted with EtOAc, washed with saturated aqueous NaHCO3, brine, and dried over Na2SO4. Concentration provides the title compound that is carried on to next step without further purification. MS (ESI) m/z 306.1 (M+1).

출처