反应 #49199

反应方程式

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

溶剂

tetrahydrofuran

THF

MeOH CHCl3

反应条件

后处理

1. 1
   workup.ADDITIONAfter the addition the reaction mixture
2. 2
   其他was brought to room temperature
3. 3
   其他The 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
   萃取was extracted with dichloromethane (3×75 mL)
7. 7
   洗涤The combined organic layer was washed with brine
8. 8
   干燥dried over sodium sulfate
9. 9
   过滤Organic layer was filtered
10. 10
    其他evaporated to dryness
11. 11
    其他Compound 74 was purified by column chromatography first
12. 12
    洗涤by eluting with dichloromethane/methanol (5%) (1.98 g, 85%)

实验过程

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%).

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