تفاعل #2028957

معادلة التفاعل

Acetaldehyde

sodium cyanoborohydride

ammonium acetate

3-phenoxyaniline

N-(tert-butoxycarbonyl)-D-prolinal

sodium triacetoxyborohydride

→

colourless oil

المردود 67.0%

(R)-2-{[Ethyl-(3-phenoxy-phenyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

المردود 67.0%

المذيبات

methanol

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 overnight at 40° C
9. 9
   استخلاصextracted with ethyl acetate (3×30 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 (SiO2: heptane/ethyl acetate=70:30)

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 methanol (8 ml). Acetaldehyde (0.134 g, 3.05 mmol), zinc chloride (0.333 g, 2.44 mmol) and sodium cyanoborohydride (0.115 g, 1.83 mmol) were added and the mixture was stirred overnight at 40° C. Saturated ammonium acetate solution (10 ml) was added and extracted with ethyl acetate (3×30 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 0.43 g (67%) of a colourless oil; MS (ISP): 397.0 ((M+H)+.).

المصدر