Réaction #87986

Équation de réaction

methyl 7-((5R)-3,3-difluoro-5-((E)-4-methyl-3-oxooct-1-en-6-yn-1-yl)-2-oxopyrrolidin-1-yl)heptanoate

cerium chloride heptahydrate

Sodium borohydride

→

title compound

Rendement 87.6%

methyl 7-((5R)-3,3-difluoro-5-((E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl)-2-oxopyrrolidin-1-yl)heptanoate

Rendement 87.6%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   AutreTo a −40° C.
2. 2
   workup.STIRRINGthe reaction was stirred for 3 hours
3. 3
   Autrequenched with equal parts water and saturated ammonium chloride
4. 4
   Températurewarmed to room temperature
5. 5
   ExtractionThe reaction mixture was extracted with ethyl acetate
6. 6
   SéchageThe combined organic phase was dried over sodium sulfate
7. 7
   Concentrationconcentrated to a cloudy white oil
8. 8
   AutreThe residue was purified by silica gel chromatography
9. 9
   LavageElution with methanol-dichloromethane (1:200 v:v)

Mode opératoire

To a −40° C. solution consisting of methyl 7-((5R)-3,3-difluoro-5-((E)-4-methyl-3-oxooct-1-en-6-yn-1-yl)-2-oxopyrrolidin-1-yl)heptanoate (76 mg, 0.20 mmol) in methanol (5 mL) was added cerium chloride heptahydrate (75 mg, 0.20 mmol) in one portion. The reaction mixture was stirred for 15 minutes, and cooled to −78° C. for 20 minutes. Sodium borohydride (15 mg, 0.40 mmol) was added and the reaction was stirred for 3 hours, quenched with equal parts water and saturated ammonium chloride and warmed to room temperature. The reaction mixture was extracted with ethyl acetate. The combined organic phase was dried over sodium sulfate and concentrated to a cloudy white oil. The residue was purified by silica gel chromatography. Elution with methanol-dichloromethane (1:200 v:v) to afford the title compound (70 mg) as a clear oil. Rf 0.50 (solvent system: 5:95 v/v methanol:dichloromethane).

Source