反応 #73339

反応方程式

imidazole

TBSCl

EtOAc

3-Amino-5-trifluoromethyl-benzoic acid

LiAlH4

NaF

→

title compound

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

溶媒

H2O

DCM

THF

THF

反応条件

後処理

1. 1
   温度The mixture is warmed
2. 2
   温度to reflux
3. 3
   workup.STIRRINGThe slurry is stirred for 10 minutes
4. 4
   温度to warm to rt
5. 5
   workup.STIRRINGstir an additional 40 min
6. 6
   ろ過The mixture is filtered
7. 7
   洗浄the solid is rinsed with EtOAc and MeOH
8. 8
   濃縮The filtrate is concentrated
9. 9
   workup.STIRRINGthe mixture is stirred at rt for 5 h
10. 10
    洗浄washed with saturated aqueous NaHCO3, brine
11. 11
    乾燥dried over Na2SO4
12. 12
    濃縮Concentration

実験手順

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).

出典