Reacción #1375833

Ecuación de reacción

ammonium chloride

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

LDA

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

→

oily product

Rendimiento 66.5%

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

Rendimiento 66.5%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was warmed to room temperature
2. 2
   workup.STIRRINGstirred for 2 hours
3. 3
   Extracciónextracted with diethyl ether
4. 4
   ExtracciónThe ether extract
5. 5
   Secadowas dried with magnesium sulfate
6. 6
   Concentraciónconcentrated by evaporation

Procedimiento

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.

Fuente