反応 #49199

反応方程式

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

溶媒

tetrahydrofuran

THF

MeOH CHCl3

反応条件

後処理

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

実験手順

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%).

出典