反応 #44621

反応方程式

4-Chlorophenyl magnesium bromide

tetrahydrofuran

(R)-5-oxopyrrolidin-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

→

title compound

(R)-2-tert-butoxycarbonylamino-5-(4-chlorophenyl)-5-oxopentanoic acid ethyl ester

溶媒

water

反応条件

後処理

1. 1
   その他The resulting reaction solution
2. 2
   温度while heating from −40° C. to 0° C. for 1 hr
3. 3
   抽出The reaction solution was extracted with ethyl acetate
4. 4
   洗浄The extract solution was washed with saturated saline
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他The residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

実験手順

4-Chlorophenyl magnesium bromide (1.0 M diethylether solution, 17.1 mL) was dropwise added to a tetrahydrofuran solution (100 mL) of (R)-5-oxopyrrolidin-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (CAS Register No. 128811-48-3, 4.0 g) over 20 min at −40° C. The resulting reaction solution was stirred while heating from −40° C. to 0° C. for 1 hr. To this solution, water was gradually added at 0° C. The reaction solution was extracted with ethyl acetate. The extract solution was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to give 5.6 g of the title compound as a colorless oily substance. The physical property values of this compound were as follows:

出典