반응 #49170

반응 방정식

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

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 (100 mL) was added slowly
5. 5
   추출was extracted with dichloromethane (3×100 mL)
6. 6
   세척The combined organic layer was washed with brine
7. 7
   건조dried over sodium sulfate
8. 8
   여과Organic layer was filtered
9. 9
   기타evaporated to dryness
10. 10
    기타Compound 3a was purified by column chromatography first
11. 11
    세척by eluting with ethyl acetate
12. 12
    기타to remove impurities
13. 13
    기타gave 14.3 g (70%)

실험 절차

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%).

출처