Réaction #49199

Équation de réaction

lithium borohydride

ethyl ester

4-Hydroxy-pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester

→

3-Hydroxy-4-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Solvants

tetrahydrofuran

THF

MeOH CHCl3

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter the addition the reaction mixture
2. 2
   Autrewas brought to room temperature
3. 3
   AutreThe reaction mixture was evaporated to dryness
4. 4
   workup.ADDITIONTo the residue 3N HCl (40 mL) was added slowly
5. 5
   workup.STIRRINGAfter stirring for 30 mins the product
6. 6
   Extractionwas extracted with dichloromethane (3×75 mL)
7. 7
   LavageThe combined organic layer was washed with brine
8. 8
   Séchagedried over sodium sulfate
9. 9
   FiltrationOrganic layer was filtered
10. 10
    Autreevaporated to dryness
11. 11
    AutreCompound 74 was purified by column chromatography first
12. 12
    Lavageby eluting with dichloromethane/methanol (5%) (1.98 g, 85%)

Mode opératoire

To the solution of lithium borohydride (0.305 g, 13 mmol) in anhydrous tetrahydrofuran (25 mL) was added a solution of ethyl ester 73 (2.69 g, 9.2 mmol) in THF (25 mL) over a period of 30 mins at 0° C. After the addition the reaction mixture was brought to room temperature and stirred further under argon. The completion of the reaction was ascertained by TLC after 4 h. (Rf=0.3 in 10% MeOH/CHCl3). The reaction mixture was evaporated to dryness and cooled to 0° C. To the residue 3N HCl (40 mL) was added slowly. After stirring for 30 mins the product was extracted with dichloromethane (3×75 mL). The combined organic layer was washed with brine and dried over sodium sulfate. Organic layer was filtered and evaporated to dryness. Compound 74 was purified by column chromatography first by eluting with dichloromethane/methanol (5%) (1.98 g, 85%).

Source