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

HRID 1173662ノート

反応式

HRID 1173662 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-417d09867df34a72be29a6c90b95114f
出典データセット
uspto-grants-2010_11
特許番号
US07834051B2

反応ノート

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