تفاعل #49170

معادلة التفاعل

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

المذيبات

tetrahydrofuran

THF

MeOH CHCl3

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter the addition the reaction mixture
2. 2
   أخرىwas brought to room temperature
3. 3
   أخرىThe reaction mixture was evaporated to dryness
4. 4
   workup.ADDITIONTo the residue 3N HCl (100 mL) was added slowly
5. 5
   استخلاصwas extracted with dichloromethane (3×100 mL)
6. 6
   غسيلThe combined organic layer was washed with brine
7. 7
   تجفيفdried over sodium sulfate
8. 8
   ترشيحOrganic layer was filtered
9. 9
   أخرىevaporated to dryness
10. 10
    أخرىCompound 3a was purified by column chromatography first
11. 11
    غسيلby eluting with ethyl acetate
12. 12
    أخرىto remove impurities
13. 13
    أخرىgave 14.3 g (70%)

الإجراء التجريبي

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%).

المصدر