Water → Rac-4-[(4r,5r)-4-hydroxy-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile

HRID 1967334ノート

反応式

HRID 1967334 の反応式
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:10]=[C:9]([N:11]2[CH:15]([CH3:16])[C:14](=[O:17])[C:13]([CH3:19])([CH3:18])[C:12]2=[O:20])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].C1COCC1.O>C1COCC1>[OH:17][C@H:14]1[C@@H:15]([CH3:16])[N:11]([C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:10]=2)[C:12](=[O:20])[C:13]1([CH3:18])[CH3:19]

参加物

5

反応物 3

HCID 962WaterHCID 595569412-(Trifluoromethyl)-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrileHCID 131725857L-SELECTRIDE tetrahydrofuran

生成物 1

HCID 67105641Rac-4-[(4r,5r)-4-hydroxy-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A solution of 2-(trifluoromethyl)-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrile (50 mg) in THF (5 mL) was cooled to −78° C., lithium tri(sec-butyl)borohydride-THF solution (0.242 mL, 1 mol/L) was added, and the mixture was stirred at −78° C. for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and the obtained solid was recrystallized from hexane-ethyl acetate to give the title compound as a colorless solid (yield: 32.2 mg, 64%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. customthe obtained solid was recrystallized from hexane-ethyl acetate

出典と根拠

ORDレコード
ord-2b2dec5baeef4333aa913a862db3bcac
出典データセット
uspto-grants-2013_04
特許番号
US08420694B2

反応ノート

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