反応 #49170

反応方程式

lithium borohydride

methyl ester

1-(6-Benzyloxycarbonylamino-hexanoyl)-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester

→

[6-(4-Hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-6-oxo-hexyl]-carbamic 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 (100 mL) was added slowly
5. 5
   抽出was extracted with dichloromethane (3×100 mL)
6. 6
   洗浄The combined organic layer was washed with brine
7. 7
   乾燥dried over sodium sulfate
8. 8
   ろ過Organic layer was filtered
9. 9
   その他evaporated to dryness
10. 10
    その他Compound 3a was purified by column chromatography first
11. 11
    洗浄by eluting with ethyl acetate
12. 12
    その他to remove impurities
13. 13
    その他gave 14.3 g (70%)

実験手順

To the solution of lithium borohydride (1.34 g) in anhydrous tetrahydrofuran (50 mL) was added a solution of methyl ester 2a in THF (50 mL) over a period of 30 mins at 0° C. After the addition the reaction mixture was brought to room temperature and stiired further under argon. The completion of the reaction was ascertained by TLC after 4 h. (Rf=0.4 in 10% MeOH/CHCl3). The reaction mixture was evaporated to dryness and cooled to 0° C. To the residue 3N HCl (100 mL) was added slowly. After stirring for 30 mins the product was extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine and dried over sodium sulfate. Organic layer was filtered and evaporated to dryness. Compound 3a was purified by column chromatography first by eluting with ethyl acetate to remove impurities followed by dichloromethane/methanol (5%) gave 14.3 g (70%).

出典