Reacción #49170

Ecuación de reacción

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

Disolventes

tetrahydrofuran

THF

MeOH CHCl3

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition the reaction mixture
2. 2
   Otrowas brought to room temperature
3. 3
   OtroThe reaction mixture was evaporated to dryness
4. 4
   workup.ADDITIONTo the residue 3N HCl (100 mL) was added slowly
5. 5
   Extracciónwas extracted with dichloromethane (3×100 mL)
6. 6
   LavadoThe combined organic layer was washed with brine
7. 7
   Secadodried over sodium sulfate
8. 8
   FiltraciónOrganic layer was filtered
9. 9
   Otroevaporated to dryness
10. 10
    OtroCompound 3a was purified by column chromatography first
11. 11
    Lavadoby eluting with ethyl acetate
12. 12
    Otroto remove impurities
13. 13
    Otrogave 14.3 g (70%)

Procedimiento

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%).

Fuente