Réaction #49170

Équation de réaction

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

Solvants

tetrahydrofuran

THF

MeOH CHCl3

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter the addition the reaction mixture
2. 2
   Autrewas brought to room temperature
3. 3
   AutreThe reaction mixture was evaporated to dryness
4. 4
   workup.ADDITIONTo the residue 3N HCl (100 mL) was added slowly
5. 5
   Extractionwas extracted with dichloromethane (3×100 mL)
6. 6
   LavageThe combined organic layer was washed with brine
7. 7
   Séchagedried over sodium sulfate
8. 8
   FiltrationOrganic layer was filtered
9. 9
   Autreevaporated to dryness
10. 10
    AutreCompound 3a was purified by column chromatography first
11. 11
    Lavageby eluting with ethyl acetate
12. 12
    Autreto remove impurities
13. 13
    Autregave 14.3 g (70%)

Mode opératoire

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%).

Source