تفاعل #45909

معادلة التفاعل

borane tetrahydrofuran

tert-Butyl {(3S)-3-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidin-3-yl}carbamate

Ethanol

triethylamine

→

compound

المردود 85.0%

tert-Butyl {(3S)-3-methyl-1-[(1R)-1-phenylethyl]pyrrolidin-3-yl}carbamate

المردود 85.0%

المذيبات

tetrahydrofuran

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGby stirring in an oil bath at 90° C. for 3 hours
3. 3
   أخرىThe reaction liquid
4. 4
   تركيزwas concentrated under reduced pressure
5. 5
   workup.DISSOLUTIONdissolved in ethyl acetate
6. 6
   غسيلwashed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine
7. 7
   تجفيفAfter drying over anhydrous sodium sulfate
8. 8
   أخرىthe insoluble matter was separated by filtration
9. 9
   أخرىthe residue obtained by concentration
10. 10
    أخرىwas purified by silica gel column chromatography (eluent, n-hexane

الإجراء التجريبي

tert-Butyl {(3S)-3-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidin-3-yl}carbamate (I-343) (500 mg, 1.57 mmol) was dissolved in tetrahydrofuran (15 ml), and with cooling with ice, borane/tetrahydrofuran complex (1.2 mol/l tetrahydrofuran solution) (3.93 ml, 4.71 mmol) was added, followed by stirring at room temperature for 17 hours. Ethanol (12 ml), triethylamine (4 ml) and water (4 ml) were added to the reaction liquid, followed by stirring in an oil bath at 90° C. for 3 hours. The reaction liquid was concentrated under reduced pressure, dissolved in ethyl acetate, and washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=2:1→1:2, v/v) to obtain the entitled compound (406 mg, 85%) as a colorless oily substance.

المصدر