تفاعل #2028960

معادلة التفاعل

(S)-2-[(4-chloro-3-methoxy-phenylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

2-methoxypropene

trifluoracetic acid

sodium triacetoxyborohydride

→

(4-Chloro-3-methoxy-phenyl)-isopropyl-(S)-1-pyrrolidin-2-ylmethyl-amine

المذيبات

sodium bicarbonate

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe mixture was extracted with ethyl acetate (3×30 ml)
2. 2
   تجفيفThe combined organic layers were dried with magnesium sulphate
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated in vacuo
5. 5
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (3 ml)
6. 6
   workup.ADDITIONtrifluoroacetic acid (3 ml) was added
7. 7
   أخرىSolvent and access trifluoroacetic acid was evaporated
8. 8
   workup.ADDITIONdiisopropylethylamine (1 ml) was added
9. 9
   أخرىthe mixture was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/heptane 1:1)
10. 10
    أخرىto yield a light yellow oil, (0.185 g, 33%)

الإجراء التجريبي

To a solution of (S)-2-[(4-chloro-3-methoxy-phenylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.68 g, 2.0 mmol) were added 2-methoxypropene (0.216 g, 3.0 mmol), trifluoracetic acid (0.228 g, 2.0 mmol) and sodium triacetoxyborohydride (0.64 g, 3.0 mmol). The mixture was stirred overnight at 60° C. Saturated sodium bicarbonate solution (10 ml) was added and the mixture was extracted with ethyl acetate (3×30 ml). The combined organic layers were dried with magnesium sulphate, filtered and concentrated in vacuo. The residue was dissolved in dichloromethane (3 ml) and trifluoroacetic acid (3 ml) was added. Solvent and access trifluoroacetic acid was evaporated, diisopropylethylamine (1 ml) was added to liberate the free base and the mixture was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/heptane 1:1) to yield a light yellow oil, (0.185 g, 33%); MS (ISP): 283.5, 285.2 ((M+H)+.).

المصدر