Réaction #45909

Équation de réaction

borane tetrahydrofuran

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

Ethanol

triethylamine

→

compound

Rendement 85.0%

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

Rendement 85.0%

Solvants

tetrahydrofuran

water

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source