반응 #49199

반응 방정식

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

용매

tetrahydrofuran

THF

MeOH CHCl3

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the addition the reaction mixture
2. 2
   기타was brought to room temperature
3. 3
   기타The 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
   추출was extracted with dichloromethane (3×75 mL)
7. 7
   세척The combined organic layer was washed with brine
8. 8
   건조dried over sodium sulfate
9. 9
   여과Organic layer was filtered
10. 10
    기타evaporated to dryness
11. 11
    기타Compound 74 was purified by column chromatography first
12. 12
    세척by eluting with dichloromethane/methanol (5%) (1.98 g, 85%)

실험 절차

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%).

출처