反応 #45909

反応方程式

borane tetrahydrofuran

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

Ethanol

triethylamine

→

compound

収率 85.0%

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

収率 85.0%

溶媒

tetrahydrofuran

water

反応条件

後処理

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

実験手順

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.

出典