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ノート

反応式

HRID 59708 の反応式
[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]

参加物

5

反応物 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

生成物 1

HCID 72949021methyl 7-((5R)-3,3-difluoro-5-((E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl)-2-oxopyrrolidin-1-yl)heptanoate収率 87.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-eb122586cd0c402ca6f9e41eb12aa96d
出典データセット
uspto-grants-2016_09
特許番号
US09440919B2

反応ノート

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