Реакция #45909

Уравнение реакции

borane tetrahydrofuran

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

Ethanol

triethylamine

→

compound

Выход 85.0%

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

Выход 85.0%

Растворители

tetrahydrofuran

water

Условия реакции

Обработка

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

Методика

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.

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