تفاعل #49190

معادلة التفاعل

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

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 (40 mL) was added slowly
5. 5
   workup.STIRRINGAfter stirring for 30 mins the product
6. 6
   استخلاصwas extracted with dichloromethane (3×75 mL)
7. 7
   غسيلThe combined organic layer was washed with brine
8. 8
   تجفيفdried over sodium sulfate
9. 9
   ترشيحOrganic layer was filtered
10. 10
    أخرىevaporated to dryness
11. 11
    أخرىCompound 63 was purified by column chromatography first
12. 12
    غسيلby eluting with dichloromethane/methanol (5%) (3.2 g, 92%)

الإجراء التجريبي

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%).

المصدر