反応 #1375833

反応方程式

ammonium chloride

(+)-(2R,8aS)-(camphorsulfonyl)oxaziridine

LDA

methyl 2-(1-methyl-3-indolyl)acetate

→

oily product

収率 66.5%

methyl 2-hydroxy-2-(1-methyl-3-indolyl)acetate

収率 66.5%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   温度The mixture was warmed to room temperature
2. 2
   workup.STIRRINGstirred for 2 hours
3. 3
   抽出extracted with diethyl ether
4. 4
   抽出The ether extract
5. 5
   乾燥was dried with magnesium sulfate
6. 6
   濃縮concentrated by evaporation

実験手順

To a solution of 2.87 millimole of LDA in 5 mL of dry tetrahydrofuran at -78° C. was added dropwise a solution of 0.53 g of methyl 2-(1-methyl-3-indolyl)acetate in 5 mL of dry tetrahyrofruan. The mixture was stirred for 30 minutes at -78° C., and then 0.9 g of (+)-(2R,8aS)-(camphorsulfonyl)oxaziridine was added. The mixture was warmed to room temperature and stirred for 2 hours. Then the mixture was poured into a solution of saturated aqueous ammonium chloride, and then extracted with diethyl ether. The ether extract was dried with magnesium sulfate and concentrated by evaporation. The residue was subjected to silica gel chromatography using a developing solution of dichloromethane/ethyl acetate (98:2 by volume) to give 0.38 g of an oily product.

出典