تفاعل #2028959

معادلة التفاعل

4-chloro-3-methoxyaniline

N-(tert-butoxycarbonyl)-L-prolinal

sodium cyanoborohydride

sodium bicarbonate

→

oil

المردود 68.0%

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

المردود 68.0%

المذيبات

methanol

acetic acid

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe mixture was extracted with ethyl acetate (3×20 ml)
2. 2
   تجفيفThe combined organic layers were dried with magnesium sulphate
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىThe residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=70:30)

الإجراء التجريبي

To a solution of 4-chloro-3-methoxyaniline (1.57 g, 10.0 mmol) in methanol (27 ml) were added acetic acid (3 ml), N-(tert-butoxycarbonyl)-L-prolinal (2.40 g, 12.05 mmol) and sodium cyanoborohydride (1.56 g, 24.1 mmol). The resulting suspension was stirred for 2 hours at room temperature. Aqueous sodium bicarbonate solution (30 ml) was added and the mixture was 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 (2.31 g, 68%); MS (ISP): 341.0, 342.9 ((M+H)+.).

المصدر