Reacción #965123

Ecuación de reacción

Diethyl methoxy borane

sodium borohydride

(S)-ethyl 6-chloro-5-hydroxy-3-oxohexanoate

→

title compound

(3R,5S)-ethyl 6-chloro-3,5-dihydroxyhexanoate

Disolventes

tetrahydrofuran

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was quenched with 50% hydrogen peroxide at 0° C
2. 2
   ExtracciónThe reaction mixture was extracted into methylene chloride
3. 3
   Lavadowashed it with 10% sodium bicarbonate
4. 4
   SecadoThe methylene chloride layer was dried with sodium sulfate
5. 5
   workup.DISTILLATIONdistilled off under reduced pressure

Procedimiento

Diethyl methoxy borane (88 ml) followed by sodium borohydride (16 grams) was added to a pre-cooled mixture of (S)-ethyl 6-chloro-5-hydroxy-3-oxohexanoate (110 grams) in tetrahydrofuran (550 ml) and methanol (220 ml) at −75° C. under nitrogen atmosphere and stirred for 2 hrs. The reaction mixture was quenched with 50% hydrogen peroxide at 0° C. The reaction mixture was extracted into methylene chloride and washed it with 10% sodium bicarbonate followed by saturated sodium chloride solution. The methylene chloride layer was dried with sodium sulfate and distilled off under reduced pressure to get the title compound.

Fuente