تفاعل #2028956

معادلة التفاعل

Trifluoroacetic acid

3-phenoxyaniline

N-(tert-butoxycarbonyl)-D-prolinal

sodium triacetoxyborohydride

sodium hydroxide

→

(3-Phenoxy-phenyl)-(R)-1-pyrrolidin-2-ylmethyl-amine

المذيبات

dichloromethane

water

1,2-dichloroethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was then cooled to room temperature
2. 2
   استخلاصextracted with ethyl acetate (3×20 ml)
3. 3
   تجفيفThe combined organic layers were dried with magnesium sulphate
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=70:30)
7. 7
   أخرىto yield a light yellow oil that
8. 8
   workup.STIRRINGthe mixture was stirred for 3 h at room temperature
9. 9
   استخلاصthe mixture was extracted with ethyl acetate (2 times 30 ml)
10. 10
    تجفيفThe combined organic layers were dried with magnesium sulphate
11. 11
    ترشيحfiltered
12. 12
    تركيزconcentrated in vacuo
13. 13
    أخرىThe residue was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate)
14. 14
    أخرىto yield a colourless oil, (0.256 g, 59%)

الإجراء التجريبي

To a solution of 3-phenoxyaniline (0.3 g, 1.62 mmol) in 1,2-dichloroethane (4 ml) were added N-(tert-butoxycarbonyl)-D-prolinal (0.322 g, 1.62 mmol) and sodium triacetoxyborohydride (0.480 g, 2.26 mmol). The resulting suspension was stirred overnight at 50° C. The mixture was then cooled to room temperature, water (8 ml) was added and extracted with ethyl acetate (3×20 ml). The combined organic layers were dried with magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=70:30) to yield a light yellow oil that was dissolved in dichloromethane (4 ml). Trifluoroacetic acid (1 ml) was added and the mixture was stirred for 3 h at room temperature. Aqueous sodium hydroxide solution (4N) was added until basic pH and the mixture was extracted with ethyl acetate (2 times 30 ml). The combined organic layers were dried with magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate) to yield a colourless oil, (0.256 g, 59%); MS (ISP): 269.1 ((M+H)+.).

المصدر