Reacción #692038

Ecuación de reacción

LiBH4

TMSCl

(2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

→

title compound

Rendimiento 55.0%

(2R,3S)-tert-butyl 3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Rendimiento 55.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe resulting mixture was stirred at room temperature overnight
2. 2
   OtroThe reaction was quenched by the careful addition of sat'd
3. 3
   workup.ADDITIONaq. NaHCO3, and the mixture was diluted with EtOAc
4. 4
   Lavadothe organic layer was washed twice with sat'd
5. 5
   Secadoaq. NaHCO3, once with brine, dried over anhydrous sodium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated in vacuo

Procedimiento

To a 0° C. suspension of LiBH4 (2.0 equiv) in THF (0.5 M) was slowly added TMSCl (4.0 equiv) by syringe. After stirring at room temperature for 30 minutes, (2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (1.0 equiv) was then added, and the resulting mixture was stirred at room temperature overnight. The reaction was quenched by the careful addition of sat'd. aq. NaHCO3, and the mixture was diluted with EtOAc, and the organic layer was washed twice with sat'd. aq. NaHCO3, once with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The title compound was isolated in 55% yield and used without further purification.

Fuente