تفاعل #73339

معادلة التفاعل

imidazole

TBSCl

EtOAc

3-Amino-5-trifluoromethyl-benzoic acid

LiAlH4

NaF

→

title compound

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

المذيبات

H2O

DCM

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture is warmed
2. 2
   درجة الحرارةto reflux
3. 3
   workup.STIRRINGThe slurry is stirred for 10 minutes
4. 4
   درجة الحرارةto warm to rt
5. 5
   workup.STIRRINGstir an additional 40 min
6. 6
   ترشيحThe mixture is filtered
7. 7
   غسيلthe solid is rinsed with EtOAc and MeOH
8. 8
   تركيزThe filtrate is concentrated
9. 9
   workup.STIRRINGthe mixture is stirred at rt for 5 h
10. 10
    غسيلwashed with saturated aqueous NaHCO3, brine
11. 11
    تجفيفdried over Na2SO4
12. 12
    تركيزConcentration

الإجراء التجريبي

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).

المصدر