Reacción #217781

Ecuación de reacción

3-(tert-Butyloxycarbonyl)pyrrolo[3,2-e]indoline-7-carboxylic acid

TFA

9-Fluorenylmethyl chloroformate

→

9

Rendimiento 84.4%

3-[(Fluoren-9-ylmethyl)oxycarbonyl]pyrrolo[3,2-e]indoline-7-carboxylic acid

Rendimiento 84.4%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTFA vas evaporated
2. 2
   workup.DISSOLUTIONthe resultant trifluoroacetate dissolved in a mixture of 11% Na2CO3 (10 mL) and 5 mL of THF
3. 3
   Extracciónextracted with ethyl ether (2×50 mL)
4. 4
   workup.ADDITIONby adding 1N HCl to pH 1-2
5. 5
   OtroPrecipitated product was collected by centrifugation
6. 6
   Lavadowashed with water
7. 7
   Otrodried under vacuum

Procedimiento

3-(tert-Butyloxycarbonyl)pyrrolo[3,2-e]indoline-7-carboxylic acid 8 (Boger et. al, J. Org. Chem. 52:1521 (1987)) (0.76 g, 2.4 mmol) was deprotected by a treatment with 5 mL of TFA for 1 h. TFA vas evaporated and the resultant trifluoroacetate dissolved in a mixture of 11% Na2CO3 (10 mL) and 5 mL of THF. 9-Fluorenylmethyl chloroformate (0.75 g, 2.9 mmol) was added and the reaction mixture was stirred for 3 h. The reaction was diluted with water (200 mL) and extracted with ethyl ether (2×50 mL). The aqueous phase was acidified by adding 1N HCl to pH 1-2. Precipitated product was collected by centrifugation, washed with water and dried under vacuum to afford 0.86 g (83%) of 9 as a yellow-gray solid.

Fuente