반응 #87986

반응 방정식

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

수율 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

수율 87.6%

용매

methanol

반응 조건

후처리

1. 1
   기타To a −40° C.
2. 2
   workup.STIRRINGthe reaction was stirred for 3 hours
3. 3
   기타quenched with equal parts water and saturated ammonium chloride
4. 4
   온도warmed to room temperature
5. 5
   추출The reaction mixture was extracted with ethyl acetate
6. 6
   건조The combined organic phase was dried over sodium sulfate
7. 7
   농축concentrated to a cloudy white oil
8. 8
   기타The residue was purified by silica gel chromatography
9. 9
   세척Elution with methanol-dichloromethane (1:200 v:v)

실험 절차

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).

출처