Реакция #49190

Уравнение реакции

lithium borohydride

ethyl ester

1-(6-Benzyloxycarbonylamino-hexanoyl)-4-hydroxy-pyrrolidine-3-carboxylic acid ethyl ester

→

[6-(3-Hydroxy-4-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 (40 mL) was added slowly
5. 5
   workup.STIRRINGAfter stirring for 30 mins the product
6. 6
   Экстракцияwas extracted with dichloromethane (3×75 mL)
7. 7
   ПромывкаThe combined organic layer was washed with brine
8. 8
   Сушкаdried over sodium sulfate
9. 9
   ФильтрацияOrganic layer was filtered
10. 10
    Другоеevaporated to dryness
11. 11
    ДругоеCompound 63 was purified by column chromatography first
12. 12
    Промывкаby eluting with dichloromethane/methanol (5%) (3.2 g, 92%)

Методика

To the solution of lithium borohydride (0.305 g, 13 mmol) in anhydrous tetrahydrofuran (25 mL) was added a solution of ethyl ester 62 (3.74 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=0.4 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 63 was purified by column chromatography first by eluting with dichloromethane/methanol (5%) (3.2 g, 92%).

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