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

HRID 59708

Reaktionsgleichung

Reaktionsgleichung von HRID 59708
[F:1][C:2]1([F:28])[CH2:6][C@H:5](/[CH:7]=[CH:8]/[C:9](=[O:16])[CH:10]([CH3:15])[CH2:11][C:12]#[C:13][CH3:14])[N:4]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:3]1=[O:27].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+]>CO>[F:28][C:2]1([F:1])[CH2:6][C@H:5](/[CH:7]=[CH:8]/[CH:9]([OH:16])[CH:10]([CH3:15])[CH2:11][C:12]#[C:13][CH3:14])[N:4]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:3]1=[O:27]

Komponenten

5

Edukt 3

HCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 90054438methyl 7-((5R)-3,3-difluoro-5-((E)-4-methyl-3-oxooct-1-en-6-yn-1-yl)-2-oxopyrrolidin-1-yl)heptanoate

Produkt 1

HCID 72949021methyl 7-((5R)-3,3-difluoro-5-((E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl)-2-oxopyrrolidin-1-yl)heptanoateAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

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).

Aufarbeitung

  1. customTo a −40° C.
  2. stirringthe reaction was stirred for 3 hours
  3. customquenched with equal parts water and saturated ammonium chloride
  4. temperaturewarmed to room temperature
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. dry with materialThe combined organic phase was dried over sodium sulfate
  7. concentrationconcentrated to a cloudy white oil
  8. customThe residue was purified by silica gel chromatography
  9. washElution with methanol-dichloromethane (1:200 v:v)

Quellen und Nachweise

ORD-Eintrag
ord-eb122586cd0c402ca6f9e41eb12aa96d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440919B2

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