Reacción #537008

Ecuación de reacción

3-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

hydrogen chloride

→

title compound

Rendimiento 80.3%

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

Rendimiento 80.3%

Disolventes

sodium hydroxide

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is cooled to 5° C. in a water ice bath
2. 2
   workup.STIRRINGThe resulting suspension is stirred further for 30 min
3. 3
   workup.DISSOLUTIONis dissolved
4. 4
   ExtracciónThis is extracted with ethyl acetate (3×100 mL)
5. 5
   LavadoThe organic layer is washed with water (2×100 mL) and brine
6. 6
   Secadodried over sodium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated to dryness
9. 9
   OtroThe resulting oil is dried under vacuum

Procedimiento

A solution of 3-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (13.29 g, 57.47 mmol) in tetrahydrofuran (130 mL) is treated with borane-methyl sulfide complex (16.06 mL, 172.41 mmol) dropwise and stirred overnight at room temperature. The mixture is cooled to 5° C. in a water ice bath and treated with 3 N aqueous hydrogen chloride solution (5 mL) dropwise until evolution of gas has ceased. The resulting suspension is stirred further for 30 min and diluted with 5 N aqueous sodium hydroxide solution until a white solid is dissolved. This is extracted with ethyl acetate (3×100 mL). The organic layer is washed with water (2×100 mL) and brine, dried over sodium sulfate, filtered, and concentrated to dryness. The resulting oil is dried under vacuum to give 10.03 g (80%) of the title compound. LC-ES/MS m/z 457.2 [2M+Na]+, TR=1.59 min.

Fuente