反应 #1340604

反应方程式

hydrochloric acid

diethyl ether

(3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-formylpyrrolidine

diiodomethane

→

title compound

(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidine

溶剂

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   workup.WAITover 8 minutes
2. 2
   其他thereof was elevated to room temperature
3. 3
   workup.WAITover 7 minutes
4. 4
   workup.STIRRINGby stirring for 1.5 hours
5. 5
   温度Subsequently, under cooling with ice
6. 6
   萃取The obtained aqueous layer was extracted with diethyl ether (100 mL×2)
7. 7
   洗涤The combined organic layer was washed by saturated brine (100 mL)
8. 8
   干燥dried over anhydrous sodium sulfate
9. 9
   过滤filtered
10. 10
    浓缩concentrated under reduced pressure
11. 11
    其他The obtained residue was purified through silica gel column chromatography (ethyl acetate:n-hexane=1:3)

实验过程

Under cooling with ice, titanium tetrachloride (3.30 mL, 1.0M toluene solution) was added to a suspension of zinc powder (1.86 g, 28.5 mmol) in tetrahydrofuran (15 mL) over 2 minutes, followed by stirring for 5 minutes at the same temperature. A solution of diiodomethane (1.15 mL, 14.3 mL) in tetrahydrofuran (5 mL) was added thereto over 8 minutes, and the resultant mixture was stirred for 15 minutes while the temperature thereof was elevated to room temperature. A solution of (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-formylpyrrolidine (900 mg, 2.58 mmol) in tetrahydrofuran (5.0 mL) was added thereto over 7 minutes, followed by stirring for 1.5 hours. Subsequently, under cooling with ice, the resultant mixture was poured to 0.5 mol/L hydrochloric acid (10 mL), followed by dilution with diethyl ether (60 mL). The obtained aqueous layer was extracted with diethyl ether (100 mL×2). The combined organic layer was washed by saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure. The obtained residue was purified through silica gel column chromatography (ethyl acetate:n-hexane=1:3), to thereby yield the title compound as a colorless oily substance (3.09 g, 31%).

来源