Реакция #49170

Уравнение реакции

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

Растворители

tetrahydrofuran

THF

MeOH CHCl3

Условия реакции

Обработка

1. 1
   workup.ADDITIONAfter the addition the reaction mixture
2. 2
   Другоеwas brought to room temperature
3. 3
   ДругоеThe reaction mixture was evaporated to dryness
4. 4
   workup.ADDITIONTo the residue 3N HCl (100 mL) was added slowly
5. 5
   Экстракцияwas extracted with dichloromethane (3×100 mL)
6. 6
   ПромывкаThe combined organic layer was washed with brine
7. 7
   Сушкаdried over sodium sulfate
8. 8
   ФильтрацияOrganic layer was filtered
9. 9
   Другоеevaporated to dryness
10. 10
    ДругоеCompound 3a was purified by column chromatography first
11. 11
    Промывкаby eluting with ethyl acetate
12. 12
    Другоеto remove impurities
13. 13
    Другоеgave 14.3 g (70%)

Методика

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%).

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